#------------------------------------------------------------------------------
#$Date: 2018-12-07 04:45:49 +0200 (Fri, 07 Dec 2018) $
#$Revision: 212431 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/19/7231957.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7231957
loop_
_publ_author_name
'Wodtke, Robert'
'Steinberg, Janine'
'Köckerling, Martin'
'Löser, Reik'
'Mamat, Constantin'
_publ_section_title
;
 NMR-based investigations of acyl-functionalized piperazines concerning
 their conformational behavior in solution
;
_journal_issue                   71
_journal_name_full               'RSC Advances'
_journal_page_first              40921
_journal_paper_doi               10.1039/C8RA09152H
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C18 H16 F2 N2 O2'
_chemical_formula_sum            'C18 H16 F2 N2 O2'
_chemical_formula_weight         330.33
_chemical_name_systematic
;
N,N'-Bis-(4F-fluorobenzoyl)-piperazine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             january-14-2018
_audit_creation_method           'ciftab-2016(M. Köckerling, 2016)'
_audit_update_record
;
2018-01-14 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.313(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5750(4)
_cell_length_b                   10.4009(7)
_cell_length_c                   11.2622(7)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      46.729
_cell_measurement_theta_min      2.6895
_cell_volume                     755.21(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            44151
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         46.731
_diffrn_reflns_theta_min         2.690
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    none
_exptl_crystal_description       cube
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_exptl_transmission_factor_max   0.74920
_exptl_transmission_factor_min   0.66450
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         6803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0781P)²+0.1170P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1647
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4519
_reflns_number_total             6803
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ra09152h2.cif
_cod_data_source_block           CM611
_cod_database_code               7231957
_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   0.977
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2014-1
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'
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
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
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'
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_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_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
