#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/87/2228764.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_2228764
loop_
_publ_author_name
'Zhou, Li-Na'
'Yan, Long'
'Zhou, Hui-Liang'
'Yang, Qing-Feng'
'Hu, Qi-Lin'
_publ_section_title
;
 2-Methoxy-4-[(4-methylpiperazin-1-yl)iminomethyl]phenol
;
_journal_coeditor_code           IM2254
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o100
_journal_paper_doi               10.1107/S1600536810051135
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C13 H19 N3 O2'
_chemical_formula_moiety         'C13 H19 N3 O2'
_chemical_formula_sum            'C13 H19 N3 O2'
_chemical_formula_weight         249.31
_chemical_melting_point          ?
_chemical_name_systematic
;
2-Methoxy-4-[(4-methylpiperazin-1-yl)iminomethyl]phenol
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.179(2)
_cell_length_b                   18.624(3)
_cell_length_c                   6.0187(10)
_cell_measurement_reflns_used    1708
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      2.00
_cell_volume                     1365.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean '9.00 cm'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7503
_diffrn_reflns_theta_full        26.67
_diffrn_reflns_theta_max         26.67
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       club-shaped
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.132
_refine_ls_extinction_coef       0.0157(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1582
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.4800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0769
_reflns_number_gt                1126
_reflns_number_total             1582
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2254.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_cell_volume        1365.1(4)
_cod_database_code               2228764
_cod_database_fobs_code          2228764
loop_
_symmetry_equiv_pos_as_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'
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.38591(18) 0.68018(10) 0.1639(4) 0.0597(7) Uani d . 1 . .
H H1 0.440(3) 0.6712(18) 0.271(7) 0.090 Uiso d . 1 . .
O O2 0.39131(16) 0.56755(10) 0.4468(4) 0.0563(6) Uani d . 1 . .
N N1 0.02060(18) 0.33961(11) 0.1024(4) 0.0441(6) Uani d . 1 . .
N N2 -0.05455(17) 0.20217(11) -0.0440(5) 0.0459(6) Uani d . 1 . .
N N3 0.09346(17) 0.39555(11) 0.1421(5) 0.0460(6) Uani d . 1 . .
C C1 0.3972(3) 0.50737(15) 0.5919(6) 0.0621(9) Uani d . 1 . .
H H1A 0.3291 0.5025 0.6707 0.093 Uiso calc R 1 . .
H H1B 0.4560 0.5143 0.6961 0.093 Uiso calc R 1 . .
H H1C 0.4107 0.4647 0.5068 0.093 Uiso calc R 1 . .
C C2 0.3147(2) 0.56473(14) 0.2784(5) 0.0406(7) Uani d . 1 . .
C C3 0.3161(2) 0.62428(13) 0.1367(5) 0.0433(7) Uani d . 1 . .
C C4 0.2429(2) 0.62631(14) -0.0381(6) 0.0500(7) Uani d . 1 . .
H H4 0.2428 0.6656 -0.1336 0.060 Uiso calc R 1 . .
C C5 0.1695(2) 0.57068(14) -0.0731(6) 0.0491(8) Uani d . 1 . .
H H5 0.1202 0.5733 -0.1908 0.059 Uiso calc R 1 . .
C C6 0.1687(2) 0.51122(14) 0.0650(5) 0.0429(7) Uani d . 1 . .
C C7 0.2418(2) 0.50933(14) 0.2442(5) 0.0439(7) Uani d . 1 . .
H H7 0.2412 0.4704 0.3408 0.053 Uiso calc R 1 . .
C C8 0.0937(2) 0.45134(14) 0.0184(6) 0.0478(8) Uani d . 1 . .
H H8A 0.0471 0.4551 -0.1155 0.057 Uiso d R 1 . .
C C9 0.0658(2) 0.27338(13) 0.1924(6) 0.0517(8) Uani d . 1 . .
H H9A 0.0887 0.2812 0.3449 0.062 Uiso calc R 1 . .
H H9B 0.1299 0.2594 0.1070 0.062 Uiso calc R 1 . .
C C10 -0.0186(2) 0.21406(15) 0.1845(6) 0.0518(8) Uani d . 1 . .
H H10A 0.0129 0.1702 0.2435 0.062 Uiso calc R 1 . .
H H10B -0.0812 0.2270 0.2759 0.062 Uiso calc R 1 . .
C C11 -0.1364(2) 0.14440(14) -0.0515(7) 0.0655(10) Uani d . 1 . .
H H11A -0.1034 0.1003 -0.0032 0.098 Uiso calc R 1 . .
H H11B -0.1628 0.1390 -0.2009 0.098 Uiso calc R 1 . .
H H11C -0.1967 0.1562 0.0446 0.098 Uiso calc R 1 . .
C C12 -0.1020(2) 0.26857(13) -0.1319(6) 0.0524(9) Uani d . 1 . .
H H12A -0.1667 0.2810 -0.0461 0.063 Uiso calc R 1 . .
H H12B -0.1247 0.2609 -0.2845 0.063 Uiso calc R 1 . .
C C13 -0.0210(2) 0.33023(15) -0.1233(6) 0.0500(9) Uani d . 1 . .
H H13A 0.0398 0.3206 -0.2233 0.060 Uiso calc R 1 . .
H H13B -0.0567 0.3741 -0.1718 0.060 Uiso calc R 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
C3 O1 H1 . . 113(2) ?
C2 O2 C1 . . 117.1(2) ?
N3 N1 C9 . . 109.2(2) ?
N3 N1 C13 . . 118.1(2) ?
C9 N1 C13 . . 112.1(2) ?
C10 N2 C12 . . 109.3(2) ?
C10 N2 C11 . . 110.1(3) ?
C12 N2 C11 . . 109.9(2) ?
C8 N3 N1 . . 120.7(2) ?
O2 C1 H1A . . 109.5 ?
O2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C7 C2 O2 . . 125.1(3) ?
C7 C2 C3 . . 120.7(3) ?
O2 C2 C3 . . 114.2(2) ?
O1 C3 C4 . . 118.5(3) ?
O1 C3 C2 . . 122.9(3) ?
C4 C3 C2 . . 118.6(2) ?
C3 C4 C5 . . 120.9(3) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C4 C5 C6 . . 120.8(3) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C7 . . 118.6(3) ?
C5 C6 C8 . . 119.9(3) ?
C7 C6 C8 . . 121.6(3) ?
C2 C7 C6 . . 120.5(3) ?
C2 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
N3 C8 C6 . . 120.5(3) ?
N3 C8 H8A . . 122.1 ?
C6 C8 H8A . . 117.3 ?
N1 C9 C10 . . 110.5(2) ?
N1 C9 H9A . . 109.5 ?
C10 C9 H9A . . 109.5 ?
N1 C9 H9B . . 109.5 ?
C10 C9 H9B . . 109.5 ?
H9A C9 H9B . . 108.1 ?
N2 C10 C9 . . 110.2(3) ?
N2 C10 H10A . . 109.6 ?
C9 C10 H10A . . 109.6 ?
N2 C10 H10B . . 109.6 ?
C9 C10 H10B . . 109.6 ?
H10A C10 H10B . . 108.1 ?
N2 C11 H11A . . 109.5 ?
N2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N2 C12 C13 . . 111.8(2) ?
N2 C12 H12A . . 109.3 ?
C13 C12 H12A . . 109.3 ?
N2 C12 H12B . . 109.3 ?
C13 C12 H12B . . 109.3 ?
H12A C12 H12B . . 107.9 ?
N1 C13 C12 . . 110.4(3) ?
N1 C13 H13A . . 109.6 ?
C12 C13 H13A . . 109.6 ?
N1 C13 H13B . . 109.6 ?
C12 C13 H13B . . 109.6 ?
H13A C13 H13B . . 108.1 ?
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
O1 C3 . 1.354(3) ?
O1 H1 . 0.94(4) ?
O2 C2 . 1.378(3) ?
O2 C1 . 1.423(3) ?
N1 N3 . 1.389(3) ?
N1 C9 . 1.456(3) ?
N1 C13 . 1.460(4) ?
N2 C10 . 1.460(4) ?
N2 C12 . 1.464(3) ?
N2 C11 . 1.468(3) ?
N3 C8 . 1.278(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C7 . 1.377(4) ?
C2 C3 . 1.399(4) ?
C3 C4 . 1.380(4) ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.385(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.399(4) ?
C6 C8 . 1.468(4) ?
C7 H7 . 0.9300 ?
C8 H8A . 0.9884 ?
C9 C10 . 1.510(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.515(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
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
O1 H1 N2 4 0.94(4) 1.88(4) 2.734(3) 151(3)
C11 H11A O2 4_544 0.96 2.67 3.311(4) 124.5
C5 H5 N1 2_564 0.93 2.67 3.460(4) 143.3
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
C9 N1 N3 C8 . . . . 155.1(3) ?
C13 N1 N3 C8 . . . . 25.5(4) ?
C1 O2 C2 C7 . . . . 2.0(4) ?
C1 O2 C2 C3 . . . . -177.6(3) ?
C7 C2 C3 O1 . . . . 179.7(3) ?
O2 C2 C3 O1 . . . . -0.7(4) ?
C7 C2 C3 C4 . . . . 0.0(4) ?
O2 C2 C3 C4 . . . . 179.6(3) ?
O1 C3 C4 C5 . . . . -179.8(3) ?
C2 C3 C4 C5 . . . . -0.1(4) ?
C3 C4 C5 C6 . . . . -0.7(5) ?
C4 C5 C6 C7 . . . . 1.5(4) ?
C4 C5 C6 C8 . . . . -177.1(3) ?
O2 C2 C7 C6 . . . . -178.7(3) ?
C3 C2 C7 C6 . . . . 0.8(4) ?
C5 C6 C7 C2 . . . . -1.6(4) ?
C8 C6 C7 C2 . . . . 177.0(3) ?
N1 N3 C8 C6 . . . . 178.2(2) ?
C5 C6 C8 N3 . . . . 178.7(3) ?
C7 C6 C8 N3 . . . . 0.1(4) ?
N3 N1 C9 C10 . . . . 171.1(3) ?
C13 N1 C9 C10 . . . . -56.0(3) ?
C12 N2 C10 C9 . . . . -59.3(3) ?
C11 N2 C10 C9 . . . . 179.9(2) ?
N1 C9 C10 N2 . . . . 58.7(3) ?
C10 N2 C12 C13 . . . . 58.0(3) ?
C11 N2 C12 C13 . . . . 178.9(3) ?
N3 N1 C13 C12 . . . . -177.9(2) ?
C9 N1 C13 C12 . . . . 53.7(3) ?
N2 C12 C13 N1 . . . . -54.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17973490
