#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:43:10 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301803 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/75/2207589.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_2207589
loop_
_publ_author_name
'Petek, Hande '
'Albayrak, Çiğdem'
'Nazan Ocak İskeleli'
'Ağar, Erbil'
'Şenel, İsmet'
_publ_section_title
;
 (E)-2-[(2-Morpholinoethylimino)methyl]phenol
;
_journal_coeditor_code           LH6532
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3990
_journal_page_last               o3991
_journal_paper_doi               10.1107/S1600536805034847
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C13 H18 N2 O2'
_chemical_formula_moiety         'C13 H18 N2 O2'
_chemical_formula_sum            'C13 H18 N2 O2'
_chemical_formula_weight         234.29
_chemical_name_systematic
;
(E)-2-[(2-morpholinoethylimino)methyl]phenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8324(4)
_cell_length_b                   9.1911(6)
_cell_length_c                   23.042(2)
_cell_measurement_reflns_used    8146
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      1.77
_cell_volume                     1235.19(16)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS-II'
_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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6052
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.523
_exptl_crystal_size_min          0.420
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.190
_refine_ls_extinction_coef       0.063(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0323
_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)+(0.0533P)²+0.0683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0853
_reflns_number_gt                1358
_reflns_number_total             1447
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6532.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1235.17(17)
_cod_database_code               2207589
_cod_database_fobs_code          2207589
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
loop_
_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_type_symbol
C1 0.2022(3) 0.07353(17) 0.06232(7) 0.0280(3) Uani d . 1 C
C2 0.2984(3) -0.04532(17) 0.03371(7) 0.0313(4) Uani d . 1 C
H2 0.4400 -0.0814 0.0455 0.038 Uiso calc R 1 H
C3 0.1841(3) -0.10963(17) -0.01199(7) 0.0318(4) Uani d . 1 C
H3 0.2495 -0.1891 -0.0307 0.038 Uiso calc R 1 H
C4 -0.0273(3) -0.05748(17) -0.03044(8) 0.0320(4) Uani d . 1 C
H4 -0.1016 -0.1002 -0.0618 0.038 Uiso calc R 1 H
C5 -0.1255(3) 0.05833(17) -0.00167(7) 0.0297(4) Uani d . 1 C
H5 -0.2679 0.0926 -0.0136 0.036 Uiso calc R 1 H
C6 -0.0153(3) 0.12521(17) 0.04504(7) 0.0265(4) Uani d . 1 C
C7 -0.1273(3) 0.24291(16) 0.07691(7) 0.0273(4) Uani d . 1 C
C8 -0.1565(3) 0.41747(17) 0.15085(7) 0.0307(4) Uani d . 1 C
H8A -0.1722 0.3879 0.1911 0.037 Uiso calc R 1 H
H8B -0.3090 0.4267 0.1344 0.037 Uiso calc R 1 H
C9 -0.0350(3) 0.56381(17) 0.14800(7) 0.0288(4) Uani d . 1 C
H9A 0.1038 0.5601 0.1712 0.035 Uiso calc R 1 H
H9B 0.0083 0.5843 0.1082 0.035 Uiso calc R 1 H
C10 -0.0833(3) 0.82278(17) 0.15845(8) 0.0358(4) Uani d . 1 C
H10A -0.0555 0.8344 0.1172 0.043 Uiso calc R 1 H
H10B 0.0623 0.8310 0.1785 0.043 Uiso calc R 1 H
C11 -0.2429(4) 0.94010(19) 0.17913(8) 0.0446(5) Uani d . 1 C
H11A -0.1742 1.0344 0.1718 0.054 Uiso calc R 1 H
H11B -0.3852 0.9348 0.1574 0.054 Uiso calc R 1 H
C12 -0.2293(3) 0.66625(18) 0.23165(7) 0.0336(4) Uani d . 1 C
H12A -0.0866 0.6717 0.2532 0.040 Uiso calc R 1 H
H12B -0.2997 0.5727 0.2396 0.040 Uiso calc R 1 H
C13 -0.3871(3) 0.7867(2) 0.25064(8) 0.0416(5) Uani d . 1 C
H13A -0.5320 0.7778 0.2303 0.050 Uiso calc R 1 H
H13B -0.4172 0.7773 0.2919 0.050 Uiso calc R 1 H
N1 -0.0288(2) 0.30694(14) 0.11905(6) 0.0292(3) Uani d . 1 N
N2 -0.1830(2) 0.67970(14) 0.16947(6) 0.0282(3) Uani d . 1 N
O1 0.3175(2) 0.13521(13) 0.10668(5) 0.0356(3) Uani d . 1 O
H1 0.2428 0.2033 0.1197 0.053 Uiso calc R 1 H
O2 -0.2908(3) 0.92647(14) 0.23932(6) 0.0456(4) Uani d . 1 O
H7 -0.285(4) 0.268(2) 0.0652(7) 0.027(4) Uiso d . 1 H
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_publ_flag
O1 C1 C2 119.16(14) ?
O1 C1 C6 121.36(14) y
C2 C1 C6 119.47(15) ?
C3 C2 C1 120.16(16) ?
C3 C2 H2 119.9 ?
C1 C2 H2 119.9 ?
C2 C3 C4 120.97(15) ?
C2 C3 H3 119.5 ?
C4 C3 H3 119.5 ?
C5 C4 C3 119.20(16) ?
C5 C4 H4 120.4 ?
C3 C4 H4 120.4 ?
C4 C5 C6 121.30(15) ?
C4 C5 H5 119.3 ?
C6 C5 H5 119.3 ?
C5 C6 C1 118.87(15) ?
C5 C6 C7 120.51(15) ?
C1 C6 C7 120.58(15) ?
N1 C7 C6 121.62(15) y
N1 C7 H7 121.4(11) ?
C6 C7 H7 116.9(11) ?
N1 C8 C9 110.90(13) ?
N1 C8 H8A 109.5 ?
C9 C8 H8A 109.5 ?
N1 C8 H8B 109.5 ?
C9 C8 H8B 109.5 ?
H8A C8 H8B 108.0 ?
N2 C9 C8 110.83(13) y
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 110.17(16) ?
N2 C10 H10A 109.6 ?
C11 C10 H10A 109.6 ?
N2 C10 H10B 109.6 ?
C11 C10 H10B 109.6 ?
H10A C10 H10B 108.1 ?
O2 C11 C10 111.62(15) ?
O2 C11 H11A 109.3 ?
C10 C11 H11A 109.3 ?
O2 C11 H11B 109.3 ?
C10 C11 H11B 109.3 ?
H11A C11 H11B 108.0 ?
N2 C12 C13 109.60(14) ?
N2 C12 H12A 109.8 ?
C13 C12 H12A 109.8 ?
N2 C12 H12B 109.8 ?
C13 C12 H12B 109.8 ?
H12A C12 H12B 108.2 ?
O2 C13 C12 111.63(15) ?
O2 C13 H13A 109.3 ?
C12 C13 H13A 109.3 ?
O2 C13 H13B 109.3 ?
C12 C13 H13B 109.3 ?
H13A C13 H13B 108.0 ?
C7 N1 C8 118.41(14) y
C9 N2 C10 111.31(13) ?
C9 N2 C12 112.32(13) ?
C10 N2 C12 108.65(13) ?
C1 O1 H1 109.5 ?
C11 O2 C13 109.61(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.348(2) y
C1 C2 1.394(2) ?
C1 C6 1.412(2) ?
C2 C3 1.379(2) ?
C2 H2 0.9300 ?
C3 C4 1.390(3) ?
C3 H3 0.9300 ?
C4 C5 1.379(2) ?
C4 H4 0.9300 ?
C5 C6 1.396(2) ?
C5 H5 0.9300 ?
C6 C7 1.461(2) ?
C7 N1 1.272(2) y
C7 H7 0.98(2) ?
C8 N1 1.457(2) y
C8 C9 1.522(2) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 N2 1.458(2) y
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 N2 1.460(2) y
C10 C11 1.502(3) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 O2 1.420(2) y
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 N2 1.463(2) y
C12 C13 1.505(2) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 O2 1.426(2) y
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
O1 H1 0.8200 ?
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
O1 H1 N1 0.82 1.85 2.5795(18) 148
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
O1 C1 C2 C3 -179.64(15)
C6 C1 C2 C3 1.5(2)
C1 C2 C3 C4 0.2(3)
C2 C3 C4 C5 -1.4(2)
C3 C4 C5 C6 0.9(2)
C4 C5 C6 C1 0.8(2)
C4 C5 C6 C7 -176.81(14)
O1 C1 C6 C5 179.18(15)
C2 C1 C6 C5 -2.0(2)
O1 C1 C6 C7 -3.2(2)
C2 C1 C6 C7 175.64(14)
C5 C6 C7 N1 -178.92(15)
C1 C6 C7 N1 3.5(2)
N1 C8 C9 N2 168.60(13)
N2 C10 C11 O2 58.6(2)
N2 C12 C13 O2 -58.96(19)
C6 C7 N1 C8 -176.49(13)
C9 C8 N1 C7 -120.44(16)
C8 C9 N2 C10 -170.92(14)
C8 C9 N2 C12 67.00(18)
C11 C10 N2 C9 178.06(15)
C11 C10 N2 C12 -57.75(18)
C13 C12 N2 C9 -178.63(15)
C13 C12 N2 C10 57.79(19)
C10 C11 O2 C13 -57.7(2)
C12 C13 O2 C11 58.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654898
2 PubChem 135459868
