#------------------------------------------------------------------------------
#$Date: 2023-06-21 12:12:42 +0300 (Wed, 21 Jun 2023) $
#$Revision: 284519 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/74/8107411.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_8107411
loop_
_publ_author_name
'Zhang, Shi-Lin'
_publ_section_title
;
 Crystal structure of
 (E)-5-(diethylamino)-2-((morpholinoimino)methyl)phenol, C15H23N3O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              259
_journal_page_last               260
_journal_paper_doi               10.1515/ncrs-2022-0600
_journal_volume                  238
_journal_year                    2023
_chemical_formula_sum            'C15 H23 N3 O2'
_chemical_formula_weight         277.36
_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   geom
_cell_angle_alpha                90
_cell_angle_beta                 92.919(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5122(15)
_cell_length_b                   7.8955(16)
_cell_length_c                   12.875(3)
_cell_measurement_reflns_used    1471
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.58
_cell_measurement_theta_min      2.58
_cell_volume                     762.7(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4703
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.090
_diffrn_reflns_theta_min         1.584
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0545
_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)+(0.0893P)²+0.2236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1629
_refine_ls_wR_factor_ref         0.1802
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2463
_reflns_number_total             3319
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0600_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               8107411
_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   0.990
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4758(5) 0.1333(5) 0.1856(3) 0.0453(8) Uani 1 1 d . . . . .
C2 C 0.3116(5) 0.0472(5) 0.1789(3) 0.0501(9) Uani 1 1 d . . . . .
C3 C 0.2083(5) 0.0426(6) 0.0870(3) 0.0531(10) Uani 1 1 d . . . . .
H3 H 0.1009 -0.0162 0.0848 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2614(5) 0.1242(5) -0.0034(3) 0.0474(9) Uani 1 1 d . . . . .
C5 C 0.4260(4) 0.2141(5) 0.0038(3) 0.0487(8) Uani 1 1 d . . . . .
H5 H 0.4651 0.2718 -0.0538 0.058 Uiso 1 1 calc R U . . .
C6 C 0.5262(5) 0.2157(5) 0.0952(3) 0.0490(9) Uani 1 1 d . . . . .
H6 H 0.6336 0.2744 0.0976 0.059 Uiso 1 1 calc R U . . .
C7 C 0.0148(5) -0.0115(7) -0.1131(3) 0.0658(12) Uani 1 1 d . U . . .
H7A H 0.0155 -0.0518 -0.1843 0.079 Uiso 1 1 calc R U . . .
H7B H 0.0366 -0.1075 -0.0672 0.079 Uiso 1 1 calc R U . . .
C8 C -0.1588(7) 0.0624(8) -0.0943(5) 0.0838(15) Uani 1 1 d . . . . .
H8A H -0.1610 0.0976 -0.0230 0.126 Uiso 1 1 calc R U . . .
H8B H -0.2504 -0.0204 -0.1086 0.126 Uiso 1 1 calc R U . . .
H8C H -0.1792 0.1586 -0.1389 0.126 Uiso 1 1 calc R U . . .
C9 C 0.2036(5) 0.2222(6) -0.1839(3) 0.0612(11) Uani 1 1 d . . . . .
H9A H 0.2528 0.3294 -0.1594 0.073 Uiso 1 1 calc R U . . .
H9B H 0.0946 0.2459 -0.2250 0.073 Uiso 1 1 calc R U . . .
C10 C 0.3351(6) 0.1378(7) -0.2526(3) 0.0708(13) Uani 1 1 d . . . . .
H10A H 0.4431 0.1130 -0.2124 0.106 Uiso 1 1 calc R U . . .
H10B H 0.3610 0.2123 -0.3087 0.106 Uiso 1 1 calc R U . . .
H10C H 0.2846 0.0345 -0.2802 0.106 Uiso 1 1 calc R U . . .
C11 C 0.5924(5) 0.1384(5) 0.2789(3) 0.0491(9) Uani 1 1 d . . . . .
H11 H 0.7024 0.1918 0.2764 0.059 Uiso 1 1 calc R U . . .
C12 C 0.6280(5) -0.0560(7) 0.5228(3) 0.0641(12) Uani 1 1 d . . . . .
H12A H 0.6564 -0.1619 0.4892 0.077 Uiso 1 1 calc R U . . .
H12B H 0.5025 -0.0577 0.5372 0.077 Uiso 1 1 calc R U . . .
C13 C 0.7389(6) -0.0388(8) 0.6235(3) 0.0725(13) Uani 1 1 d . . . . .
H13A H 0.7043 0.0633 0.6592 0.087 Uiso 1 1 calc R U . . .
H13B H 0.7164 -0.1347 0.6680 0.087 Uiso 1 1 calc R U . . .
C14 C 0.9553(7) 0.1102(9) 0.5422(4) 0.0823(16) Uani 1 1 d . . . . .
H14A H 1.0818 0.1160 0.5305 0.099 Uiso 1 1 calc R U . . .
H14B H 0.9229 0.2126 0.5783 0.099 Uiso 1 1 calc R U . . .
C15 C 0.8515(6) 0.1024(7) 0.4378(3) 0.0677(13) Uani 1 1 d . . . . .
H15A H 0.8714 0.2052 0.3988 0.081 Uiso 1 1 calc R U . . .
H15B H 0.8925 0.0072 0.3979 0.081 Uiso 1 1 calc R U . . .
N1 N 0.1610(4) 0.1191(6) -0.0943(3) 0.0659(11) Uani 1 1 d . U . . .
N2 N 0.5485(4) 0.0714(4) 0.3649(2) 0.0529(8) Uani 1 1 d . . . . .
N3 N 0.6628(4) 0.0838(5) 0.4542(2) 0.0541(8) Uani 1 1 d . . . . .
O1 O 0.2486(4) -0.0338(5) 0.2630(2) 0.0697(9) Uani 1 1 d . . . . .
H1 H 0.3118 -0.0108 0.3149 0.105 Uiso 1 1 calc R U . . .
O2 O 0.9225(4) -0.0313(5) 0.6053(2) 0.0697(9) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 116.5(3) . .
C6 C1 C11 119.9(3) . .
C2 C1 C11 123.7(3) . .
O1 C2 C3 117.7(3) . .
O1 C2 C1 121.1(3) . .
C3 C2 C1 121.2(3) . .
C2 C3 C4 121.7(3) . .
C2 C3 H3 119.1 . .
C4 C3 H3 119.1 . .
N1 C4 C3 122.0(3) . .
N1 C4 C5 120.8(3) . .
C3 C4 C5 117.1(3) . .
C6 C5 C4 120.0(3) . .
C6 C5 H5 120.0 . .
C4 C5 H5 120.0 . .
C5 C6 C1 123.5(3) . .
C5 C6 H6 118.3 . .
C1 C6 H6 118.3 . .
C8 C7 N1 110.3(5) . .
C8 C7 H7A 109.6 . .
N1 C7 H7A 109.6 . .
C8 C7 H7B 109.6 . .
N1 C7 H7B 109.6 . .
H7A C7 H7B 108.1 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N1 C9 C10 113.1(4) . .
N1 C9 H9A 109.0 . .
C10 C9 H9A 109.0 . .
N1 C9 H9B 109.0 . .
C10 C9 H9B 109.0 . .
H9A C9 H9B 107.8 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N2 C11 C1 122.1(3) . .
N2 C11 H11 118.9 . .
C1 C11 H11 118.9 . .
N3 C12 C13 110.2(4) . .
N3 C12 H12A 109.6 . .
C13 C12 H12A 109.6 . .
N3 C12 H12B 109.6 . .
C13 C12 H12B 109.6 . .
H12A C12 H12B 108.1 . .
O2 C13 C12 111.2(3) . .
O2 C13 H13A 109.4 . .
C12 C13 H13A 109.4 . .
O2 C13 H13B 109.4 . .
C12 C13 H13B 109.4 . .
H13A C13 H13B 108.0 . .
O2 C14 C15 112.3(4) . .
O2 C14 H14A 109.1 . .
C15 C14 H14A 109.1 . .
O2 C14 H14B 109.1 . .
C15 C14 H14B 109.1 . .
H14A C14 H14B 107.9 . .
N3 C15 C14 109.7(4) . .
N3 C15 H15A 109.7 . .
C14 C15 H15A 109.7 . .
N3 C15 H15B 109.7 . .
C14 C15 H15B 109.7 . .
H15A C15 H15B 108.2 . .
C4 N1 C9 121.9(3) . .
C4 N1 C7 121.5(3) . .
C9 N1 C7 116.0(3) . .
C11 N2 N3 120.3(3) . .
N2 N3 C12 108.9(3) . .
N2 N3 C15 116.7(3) . .
C12 N3 C15 112.0(3) . .
C2 O1 H1 109.5 . .
C14 O2 C13 109.2(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.403(5) .
C1 C2 1.407(5) .
C1 C11 1.451(5) .
C2 O1 1.363(5) .
C2 C3 1.382(5) .
C3 C4 1.406(5) .
C3 H3 0.9300 .
C4 N1 1.360(5) .
C4 C5 1.424(5) .
C5 C6 1.364(5) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.461(6) .
C7 N1 1.517(6) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 N1 1.461(5) .
C9 C10 1.513(6) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 N2 1.285(5) .
C11 H11 0.9300 .
C12 N3 1.445(5) .
C12 C13 1.511(5) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 O2 1.412(5) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 O2 1.411(6) .
C14 C15 1.520(6) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 N3 1.451(5) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
N2 N3 1.404(4) .
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
_geom_hbond_site_symmetry_A
O1 H1 N2 0.82 1.97 2.681(4) 144.6 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 O1 -178.6(4) . . . .
C11 C1 C2 O1 2.2(6) . . . .
C6 C1 C2 C3 1.1(6) . . . .
C11 C1 C2 C3 -178.1(4) . . . .
O1 C2 C3 C4 179.2(4) . . . .
C1 C2 C3 C4 -0.5(6) . . . .
C2 C3 C4 N1 179.5(4) . . . .
C2 C3 C4 C5 -0.6(6) . . . .
N1 C4 C5 C6 -179.0(4) . . . .
C3 C4 C5 C6 1.2(6) . . . .
C4 C5 C6 C1 -0.6(6) . . . .
C2 C1 C6 C5 -0.6(6) . . . .
C11 C1 C6 C5 178.7(4) . . . .
C6 C1 C11 N2 176.8(4) . . . .
C2 C1 C11 N2 -4.0(6) . . . .
N3 C12 C13 O2 -57.7(6) . . . .
O2 C14 C15 N3 55.5(6) . . . .
C3 C4 N1 C9 171.6(4) . . . .
C5 C4 N1 C9 -8.2(7) . . . .
C3 C4 N1 C7 -17.2(7) . . . .
C5 C4 N1 C7 163.0(4) . . . .
C10 C9 N1 C4 87.0(5) . . . .
C10 C9 N1 C7 -84.7(5) . . . .
C8 C7 N1 C4 99.0(5) . . . .
C8 C7 N1 C9 -89.3(5) . . . .
C1 C11 N2 N3 -178.0(4) . . . .
C11 N2 N3 C12 -154.8(4) . . . .
C11 N2 N3 C15 -26.7(5) . . . .
C13 C12 N3 N2 -175.6(4) . . . .
C13 C12 N3 C15 53.8(5) . . . .
C14 C15 N3 N2 -178.8(4) . . . .
C14 C15 N3 C12 -52.3(5) . . . .
C15 C14 O2 C13 -59.6(6) . . . .
C12 C13 O2 C14 60.2(6) . . . .
