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#$Date: 2020-03-06 08:26:34 +0200 (Fri, 06 Mar 2020) $
#$Revision: 249116 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/33/2243308.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_2243308
loop_
_publ_author_name
'Kiran Kumar, Haruvegowda'
'Yathirajan, Hemmige S.'
'Harish Chinthal, Chayanna'
'Foro, Sabine'
'Glidewell, Christopher'
_publ_section_title
;
 Crystal structures of the recreational drug
 N-(4-methoxyphenyl)piperazine (MeOPP) and three of its salts
;
_journal_coeditor_code           ZL2772
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              488
_journal_page_last               495
_journal_paper_doi               10.1107/S2056989020002844
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C11 H16 N2 O'
_chemical_formula_moiety         'C11 H16 N2 O'
_chemical_formula_sum            'C11 H16 N2 O'
_chemical_formula_weight         192.26
_chemical_name_systematic
;
N-(4-Methoxyphenyl)piperazine
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9683(7)
_cell_length_b                   7.9683(8)
_cell_length_c                   18.975(2)
_cell_measurement_reflns_used    1984
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.706
_cell_measurement_theta_min      2.772
_cell_volume                     1053.60(19)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL-2014 (Sheldrick, 2015b) and PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur
with Sapphire CCD
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4066
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.706
_diffrn_reflns_theta_min         2.772
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.400
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.116
_refine_ls_abs_structure_details
;
Flack x determined using 546 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1984
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0355
_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)+(0.0466P)²+0.0420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                1545
_reflns_number_total             1984
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zl2772sup1.cif
_cod_data_source_block           I
_cod_database_code               2243308
_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   0.963
_shelx_estimated_absorpt_t_max   0.969
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -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
N N1 0.7092(4) 0.4549(3) 0.62326(14) 0.0784(6) Uani d 1 . .
H H1 0.790(5) 0.480(4) 0.6597(19) 0.094 Uiso d 1 . .
C C2 0.8074(4) 0.4800(3) 0.55762(17) 0.0709(7) Uani d 1 . .
H H2A 0.9239 0.4134 0.5568 0.085 Uiso calc 1 . .
H H2B 0.8428 0.5972 0.5528 0.085 Uiso calc 1 . .
C C3 0.6799(3) 0.4296(3) 0.49739(15) 0.0617(6) Uani d 1 . .
H H3A 0.7453 0.4509 0.4532 0.074 Uiso calc 1 . .
H H3B 0.6531 0.3103 0.5002 0.074 Uiso calc 1 . .
N N4 0.4997(3) 0.5231(2) 0.49904(11) 0.0502(4) Uani d 1 . .
C C5 0.4049(3) 0.5099(3) 0.56726(13) 0.0582(6) Uani d 1 . .
H H5A 0.3622 0.3954 0.5746 0.070 Uiso calc 1 . .
H H5B 0.2930 0.5823 0.5680 0.070 Uiso calc 1 . .
C C6 0.5390(4) 0.5596(4) 0.62554(15) 0.0716(7) Uani d 1 . .
H H6A 0.5749 0.6765 0.6203 0.086 Uiso calc 1 . .
H H6B 0.4754 0.5464 0.6707 0.086 Uiso calc 1 . .
C C21 0.3791(3) 0.5080(2) 0.43961(12) 0.0465(5) Uani d 1 . .
C C22 0.4222(3) 0.4034(3) 0.38284(13) 0.0568(6) Uani d 1 . .
H H22 0.5303 0.3351 0.3848 0.068 Uiso calc 1 . .
C C23 0.3067(4) 0.3998(3) 0.32390(13) 0.0614(6) Uani d 1 . .
H H23 0.3391 0.3300 0.2864 0.074 Uiso calc 1 . .
C C24 0.1445(4) 0.4975(3) 0.31948(13) 0.0568(7) Uani d 1 . .
C C25 0.0979(3) 0.6002(3) 0.37552(14) 0.0567(6) Uani d 1 . .
H H25 -0.0117 0.6665 0.3736 0.068 Uiso calc 1 . .
C C26 0.2136(3) 0.6042(2) 0.43401(13) 0.0539(6) Uani d 1 . .
H H26 0.1799 0.6739 0.4713 0.065 Uiso calc 1 . .
O O24 0.0395(3) 0.4861(2) 0.25830(11) 0.0798(6) Uani d 1 . .
C C27 -0.1153(4) 0.5990(5) 0.2494(2) 0.1065(12) Uani d 1 . .
H H27A -0.1652 0.5889 0.2024 0.160 Uiso calc 1 . .
H H27B -0.0713 0.7118 0.2570 0.160 Uiso calc 1 . .
H H27C -0.2145 0.5731 0.2828 0.160 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'
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
C2 N1 C6 . . 109.6(2) ?
C2 N1 H1 . . 110(2) ?
C6 N1 H1 . . 111(2) ?
N1 C2 C3 . . 109.9(2) ?
N1 C2 H2A . . 109.7 ?
C3 C2 H2A . . 109.7 ?
N1 C2 H2B . . 109.7 ?
C3 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
N4 C3 C2 . . 110.8(2) ?
N4 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
N4 C3 H3B . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C21 N4 C5 . . 115.72(15) ?
C21 N4 C3 . . 116.8(2) ?
C5 N4 C3 . . 111.8(2) ?
N4 C5 C6 . . 110.71(18) ?
N4 C5 H5A . . 109.5 ?
C6 C5 H5A . . 109.5 ?
N4 C5 H5B . . 109.5 ?
C6 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
N1 C6 C5 . . 109.6(2) ?
N1 C6 H6A . . 109.7 ?
C5 C6 H6A . . 109.7 ?
N1 C6 H6B . . 109.7 ?
C5 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
C26 C21 C22 . . 116.7(2) ?
C26 C21 N4 . . 120.58(19) ?
C22 C21 N4 . . 122.66(19) ?
C23 C22 C21 . . 120.9(2) ?
C23 C22 H22 . . 119.6 ?
C21 C22 H22 . . 119.6 ?
C24 C23 C22 . . 121.2(2) ?
C24 C23 H23 . . 119.4 ?
C22 C23 H23 . . 119.4 ?
O24 C24 C23 . . 116.8(2) ?
O24 C24 C25 . . 124.4(2) ?
C23 C24 C25 . . 118.8(2) ?
C26 C25 C24 . . 119.9(2) ?
C26 C25 H25 . . 120.0 ?
C24 C25 H25 . . 120.0 ?
C25 C26 C21 . . 122.5(2) ?
C25 C26 H26 . . 118.8 ?
C21 C26 H26 . . 118.8 ?
C24 O24 C27 . . 117.7(2) ?
O24 C27 H27A . . 109.5 ?
O24 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
O24 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
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
N1 C2 . 1.435(4) ?
N1 C6 . 1.451(4) ?
N1 H1 . 0.91(4) ?
C2 C3 . 1.502(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 N4 . 1.460(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
N4 C21 . 1.411(3) ?
N4 C5 . 1.457(3) ?
C5 C6 . 1.501(4) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C21 C26 . 1.389(3) ?
C21 C22 . 1.395(3) ?
C22 C23 . 1.378(4) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.375(3) ?
C23 H23 . 0.9300 ?
C24 O24 . 1.375(3) ?
C24 C25 . 1.380(4) ?
C25 C26 . 1.372(4) ?
C25 H25 . 0.9300 ?
C26 H26 . 0.9300 ?
O24 C27 . 1.415(4) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
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
N1 H1 O24 2_665 0.91(4) 2.23(4) 3.139(3) 171(3) 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
C6 N1 C2 C3 . . . . -61.6(3) ?
N1 C2 C3 N4 . . . . 57.0(3) ?
C2 C3 N4 C21 . . . . 170.30(19) ?
C2 C3 N4 C5 . . . . -53.1(3) ?
C21 N4 C5 C6 . . . . -169.38(19) ?
C3 N4 C5 C6 . . . . 53.5(2) ?
C2 N1 C6 C5 . . . . 61.8(3) ?
N4 C5 C6 N1 . . . . -57.4(3) ?
C5 N4 C21 C26 . . . . 50.9(2) ?
C3 N4 C21 C26 . . . . -174.17(19) ?
C5 N4 C21 C22 . . . . -131.9(2) ?
C3 N4 C21 C22 . . . . 3.0(3) ?
C26 C21 C22 C23 . . . . 1.3(3) ?
N4 C21 C22 C23 . . . . -176.0(2) ?
C21 C22 C23 C24 . . . . -0.8(3) ?
C22 C23 C24 O24 . . . . 179.5(2) ?
C22 C23 C24 C25 . . . . -0.1(3) ?
O24 C24 C25 C26 . . . . -179.1(2) ?
C23 C24 C25 C26 . . . . 0.5(3) ?
C24 C25 C26 C21 . . . . 0.1(3) ?
C22 C21 C26 C25 . . . . -1.0(3) ?
N4 C21 C26 C25 . . . . 176.40(19) ?
C23 C24 O24 C27 . . . . -173.1(3) ?
C25 C24 O24 C27 . . . . 6.6(4) ?

_cod_database_fobs_code 2243308
