#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/80/2008082.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_2008082
loop_
_publ_author_name
'S.Shanmuga Sundara Raj'
R.Thirumurugan
G.Shanmugam
'Hoong-Kun Fun'
J.Manonmani
M.Kandaswamy
_publ_section_title
;2-Hydroxy-5-methyl-3-(morpholinomethyl)benzaldehyde, (I), and
 4,4'-dimethyl-6,6'-bis(morpholinomethyl)-2,2'-(ethylenedinitrilodimethylidyne)diphenol,
 (II)
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              94
_journal_page_last               97
_journal_paper_doi               10.1107/S0108270198010750
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.28
_chemical_melting_point          448.15
_chemical_name_systematic
;
2-Hydroxy-5-methyl-3-(morpholinomethyl)benzaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 91.8460(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.31720(10)
_cell_length_b                   15.3099(3)
_cell_length_c                   15.34060(10)
_cell_measurement_reflns_used    4735
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.22
_cell_measurement_theta_min      1.37
_cell_volume                     1248.17(3)
_computing_cell_refinement       'SAINT (Siemens, 1996b)'
_computing_data_collection       'SMART (Siemens, 1996a)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL & PARST (Nardelli, 1995)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1996)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device
;
Siemens SMART CCD area detector diffractometer
;
_diffrn_measurement_method       'ω scans'
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7859
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.201
_refine_ls_extinction_coef       0.039(5)
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_all   1.070
_refine_ls_goodness_of_fit_obs   1.143
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_restrained_S_obs      1.143
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_obs          0.0490
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0663P)²+0.2732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1487
_refine_ls_wR_factor_obs         0.1355
_reflns_number_observed          2094
_reflns_number_total             2832
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ha1231.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '175\%C' was changed to '448.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '175\%C' was changed to '448.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.2732P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0663P)^2^+0.2732P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2008082
_cod_database_fobs_code          2008082
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.2447(3) 0.55635(10) 0.20868(9) 0.0442(4) Uani d . 1 . C
C2 0.4111(3) 0.62699(10) 0.22080(10) 0.0465(4) Uani d . 1 . C
C3 0.5867(3) 0.62316(12) 0.28910(11) 0.0532(4) Uani d . 1 . C
H3A 0.6999(3) 0.66908(12) 0.29643(11) 0.064 Uiso calc R 1 . H
C4 0.6014(3) 0.55345(12) 0.34743(10) 0.0551(4) Uani d . 1 . C
C5 0.4348(3) 0.48554(12) 0.33454(11) 0.0546(4) Uani d . 1 . C
H5A 0.4414(3) 0.43828(12) 0.37264(11) 0.065 Uiso calc R 1 . H
C6 0.2559(3) 0.48564(11) 0.26583(10) 0.0487(4) Uani d . 1 . C
O7 0.0739(2) 0.55552(9) 0.14110(8) 0.0575(3) Uani d . 1 . O
C8 0.7918(4) 0.5526(2) 0.42251(13) 0.0777(6) Uani d . 1 . C
H8A 0.8914(4) 0.6049(2) 0.42119(13) 0.117 Uiso calc R 1 . H
H8B 0.8993(4) 0.5026(2) 0.41757(13) 0.117 Uiso calc R 1 . H
H8C 0.7060(4) 0.5498(2) 0.47654(13) 0.117 Uiso calc R 1 . H
C9 0.3906(4) 0.70645(11) 0.16330(12) 0.0576(4) Uani d . 1 . C
H9A 0.2566(4) 0.74366(11) 0.18331(12) 0.069 Uiso calc R 1 . H
H9B 0.5466(4) 0.73923(11) 0.16801(12) 0.069 Uiso calc R 1 . H
N10 0.3389(2) 0.68306(8) 0.07112(8) 0.0476(3) Uani d . 1 . N
C11 0.5541(3) 0.63968(12) 0.03305(12) 0.0589(5) Uani d . 1 . C
H11A 0.5971(3) 0.58762(12) 0.06635(12) 0.071 Uiso calc R 1 . H
H11B 0.6985(3) 0.67846(12) 0.03519(12) 0.071 Uiso calc R 1 . H
C12 0.4911(5) 0.61535(14) -0.05958(13) 0.0736(6) Uani d . 1 . C
H12A 0.6339(5) 0.58595(14) -0.08424(13) 0.088 Uiso calc R 1 . H
H12B 0.3502(5) 0.57508(14) -0.06118(13) 0.088 Uiso calc R 1 . H
O13 0.4285(3) 0.69024(10) -0.11065(9) 0.0814(5) Uani d . 1 . O
C14 0.2227(4) 0.73414(15) -0.07489(13) 0.0737(6) Uani d . 1 . C
H14A 0.0762(4) 0.69641(15) -0.07815(13) 0.088 Uiso calc R 1 . H
H14B 0.1849(4) 0.78596(15) -0.10924(13) 0.088 Uiso calc R 1 . H
C15 0.2739(4) 0.76016(11) 0.01821(12) 0.0611(5) Uani d . 1 . C
H15A 0.4116(4) 0.80171(11) 0.02139(12) 0.073 Uiso calc R 1 . H
H15B 0.1260(4) 0.78815(11) 0.04095(12) 0.073 Uiso calc R 1 . H
C16 0.0799(4) 0.41244(14) 0.25634(13) 0.0666(5) Uani d . 1 . C
H16A -0.0394(4) 0.41415(14) 0.21066(13) 0.080 Uiso calc R 1 . H
O17 0.0807(3) 0.34995(11) 0.30445(13) 0.0968(6) Uani d . 1 . O
H7 0.117(5) 0.6036(18) 0.1096(17) 0.100(8) 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 0.0016 '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_publ_flag
O7 C1 C6 119.20(14) ?
O7 C1 C2 120.75(14) ?
C6 C1 C2 120.05(14) ?
C3 C2 C1 118.33(15) ?
C3 C2 C9 120.9(2) ?
C1 C2 C9 120.75(14) ?
C2 C3 C4 122.8(2) ?
C2 C3 H3A 118.60(10) ?
C4 C3 H3A 118.60(10) ?
C5 C4 C3 117.65(15) ?
C5 C4 C8 121.1(2) ?
C3 C4 C8 121.3(2) ?
C4 C5 C6 121.8(2) ?
C4 C5 H5A 119.09(10) ?
C6 C5 H5A 119.09(10) ?
C1 C6 C5 119.3(2) ?
C1 C6 C16 121.2(2) ?
C5 C6 C16 119.5(2) ?
C1 O7 H7 102.9(16) ?
C4 C8 H8A 109.47(13) ?
C4 C8 H8B 109.47(12) ?
H8A C8 H8B 109.5 ?
C4 C8 H8C 109.47(11) ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
N10 C9 C2 111.91(13) yes
N10 C9 H9A 109.23(9) ?
C2 C9 H9A 109.23(9) ?
N10 C9 H9B 109.23(9) ?
C2 C9 H9B 109.23(9) ?
H9A C9 H9B 107.9 ?
C11 N10 C15 108.55(13) yes
C11 N10 C9 111.65(14) yes
C15 N10 C9 111.60(13) yes
N10 C11 C12 109.8(2) yes
N10 C11 H11A 109.71(9) ?
C12 C11 H11A 109.71(11) ?
N10 C11 H11B 109.71(9) ?
C12 C11 H11B 109.71(12) ?
H11A C11 H11B 108.2 ?
O13 C12 C11 111.3(2) yes
O13 C12 H12A 109.36(10) ?
C11 C12 H12A 109.36(11) ?
O13 C12 H12B 109.36(12) ?
C11 C12 H12B 109.36(12) ?
H12A C12 H12B 108.0 ?
C14 O13 C12 109.91(14) yes
O13 C14 C15 112.2(2) yes
O13 C14 H14A 109.16(12) ?
C15 C14 H14A 109.16(12) ?
O13 C14 H14B 109.16(10) ?
C15 C14 H14B 109.16(10) ?
H14A C14 H14B 107.9 ?
N10 C15 C14 110.21(15) yes
N10 C15 H15A 109.62(10) ?
C14 C15 H15A 109.62(12) ?
N10 C15 H15B 109.62(9) ?
C14 C15 H15B 109.62(11) ?
H15A C15 H15B 108.1 ?
O17 C16 C6 123.7(2) yes
O17 C16 H16A 118.13(13) ?
C6 C16 H16A 118.13(10) ?
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
C1 O7 . 1.356(2) yes
C1 C6 . 1.393(2) ?
C1 C2 . 1.406(2) ?
C2 C3 . 1.382(2) ?
C2 C9 . 1.504(2) ?
C3 C4 . 1.393(2) ?
C3 H3A . 0.93 ?
C4 C5 . 1.376(3) ?
C4 C8 . 1.509(2) ?
C5 C6 . 1.397(2) ?
C5 H5A . 0.93 ?
C6 C16 . 1.464(3) ?
O7 H7 . 0.91(3) ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 N10 . 1.476(2) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
N10 C11 . 1.461(2) yes
N10 C15 . 1.468(2) yes
C11 C12 . 1.496(3) yes
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 O13 . 1.422(2) yes
C12 H12A . 0.97 ?
C12 H12B . 0.97 ?
O13 C14 . 1.410(2) yes
C14 C15 . 1.499(3) yes
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C16 O17 . 1.208(2) yes
C16 H16A . 0.93 ?
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
O7 H7 N10 1_555 0.91(3) 1.81(3) 2.655(2) 153(2) yes
C9 H9A O17 2_555 0.97(2) 2.43(3) 3.381(3) 165(2) yes
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_publ_flag
O7 C1 C2 C3 -177.95(14) ?
C6 C1 C2 C3 1.3(2) ?
O7 C1 C2 C9 4.7(2) ?
C6 C1 C2 C9 -175.98(14) ?
C1 C2 C3 C4 -1.6(2) ?
C9 C2 C3 C4 175.7(2) ?
C2 C3 C4 C5 1.0(2) ?
C2 C3 C4 C8 -178.5(2) ?
C3 C4 C5 C6 -0.1(2) ?
C8 C4 C5 C6 179.4(2) ?
O7 C1 C6 C5 178.81(14) ?
C2 C1 C6 C5 -0.5(2) ?
O7 C1 C6 C16 -2.6(2) ?
C2 C1 C6 C16 178.1(2) ?
C4 C5 C6 C1 -0.1(2) ?
C4 C5 C6 C16 -178.7(2) ?
C3 C2 C9 N10 141.7(2) ?
C1 C2 C9 N10 -41.1(2) ?
C2 C9 N10 C11 -68.7(2) ?
C2 C9 N10 C15 169.64(15) ?
C15 N10 C11 C12 -57.9(2) yes
C9 N10 C11 C12 178.67(15) ?
N10 C11 C12 O13 59.7(2) yes
C11 C12 O13 C14 -58.4(2) yes
C12 O13 C14 C15 57.2(2) yes
C11 N10 C15 C14 56.5(2) yes
C9 N10 C15 C14 180.0(2) ?
O13 C14 C15 N10 -57.2(2) yes
C1 C6 C16 O17 -179.5(2) ?
C5 C6 C16 O17 -0.9(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21105617
