#------------------------------------------------------------------------------
#$Date: 2022-09-20 11:32:02 +0300 (Tue, 20 Sep 2022) $
#$Revision: 277994 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/94/1559475.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_1559475
loop_
_publ_author_name
'Hajib, Sara'
'Boukhssas, Salaheddine'
'Aouine, Younas'
'Alami, Anouar'
'Faraj, Hassane'
'Zouihri, Hafid'
'El Bali, Brahim'
'Lachkar, Mohammed'
_publ_section_title
;
 4,4-Bis(hydroxymethyl)-2-phenyl-2-oxazoline
;
_journal_issue                   4
_journal_name_full               Molbank
_journal_page_first              M1163
_journal_paper_doi               10.3390/M1163
_journal_volume                  2020
_journal_year                    2020
_chemical_formula_moiety         'C11 H13 N O3'
_chemical_formula_sum            'C11 H13 N O3'
_chemical_formula_weight         207.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-09-04 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 114.2670(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.8302(5)
_cell_length_b                   10.1380(3)
_cell_length_c                   14.2916(7)
_cell_measurement_reflns_used    325
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.2
_cell_measurement_theta_min      1.7
_cell_volume                     2090.95(14)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD detector'
_diffrn_measurement_method       'ω and φ'
_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  0.0262
_diffrn_reflns_av_unetI/netI     0.0084
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            42887
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         4.020
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0107(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0439
_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)+(0.0669P)²+1.6455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1766
_reflns_number_total             2053
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            s2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;

2022-09-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C22 H26 N2 O6'
_cod_original_formula_weight         414.45
_cod_original_formula_moiety         'C22 H26 N2 O6'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1559475
_publcif_datablock.id            {c3fb45ab-1843-4df9-9ca6-1c95715c8c35}
_shelx_shelxl_version_number     2018/3
_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.
;
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_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'
'-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_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
N1 N 0.04485(8) 0.34212(12) 0.16387(9) 0.0296(3) Uani 1 1 d . . . . .
O3 O 0.15988(7) 0.19324(11) 0.20555(9) 0.0392(3) Uani 1 1 d . . . . .
C7 C 0.06832(9) 0.22189(14) 0.16696(10) 0.0283(3) Uani 1 1 d . . . . .
C10 C 0.13038(9) 0.42246(15) 0.19933(10) 0.0317(4) Uani 1 1 d . . . . .
O2 O 0.12474(8) 0.45370(13) 0.36665(8) 0.0434(3) Uani 1 1 d D . . . .
C6 C 0.00497(10) 0.10874(14) 0.13146(11) 0.0322(4) Uani 1 1 d . . . . .
C9 C 0.20744(10) 0.31760(16) 0.23873(12) 0.0389(4) Uani 1 1 d . . . . .
H9A H 0.252206 0.330998 0.209381 0.047 Uiso 1 1 calc R U . . .
H9B H 0.239356 0.320805 0.312945 0.047 Uiso 1 1 calc R U . . .
C11 C 0.13243(12) 0.51797(16) 0.28266(12) 0.0391(4) Uani 1 1 d . . . . .
H11A H 0.189989 0.567321 0.307247 0.047 Uiso 1 1 calc R U . . .
H11B H 0.081871 0.580358 0.253166 0.047 Uiso 1 1 calc R U . . .
C12 C 0.13225(12) 0.49979(16) 0.10898(12) 0.0413(4) Uani 1 1 d . . . . .
H12A H 0.077561 0.554988 0.079201 0.050 Uiso 1 1 calc R U . . .
H12B H 0.186596 0.555998 0.131548 0.050 Uiso 1 1 calc R U . . .
O1 O 0.13448(10) 0.40795(13) 0.03560(10) 0.0560(4) Uani 1 1 d D . . . .
C1 C -0.09000(11) 0.12971(18) 0.08278(13) 0.0435(4) Uani 1 1 d . . . . .
H1 H -0.113213 0.215276 0.073207 0.052 Uiso 1 1 calc R U . . .
C5 C 0.03819(13) -0.01964(17) 0.14381(15) 0.0473(4) Uani 1 1 d . . . . .
H5 H 0.101559 -0.035554 0.176206 0.057 Uiso 1 1 calc R U . . .
C3 C -0.11663(16) -0.1026(2) 0.06086(17) 0.0623(6) Uani 1 1 d . . . . .
H3 H -0.157301 -0.173405 0.037400 0.075 Uiso 1 1 calc R U . . .
C2 C -0.15001(13) 0.0244(2) 0.04859(16) 0.0567(5) Uani 1 1 d . . . . .
H2 H -0.213541 0.039311 0.016986 0.068 Uiso 1 1 calc R U . . .
C4 C -0.02314(16) -0.12397(19) 0.10783(17) 0.0632(6) Uani 1 1 d . . . . .
H4 H -0.000484 -0.209777 0.115702 0.076 Uiso 1 1 calc R U . . .
H1O H 0.1341(18) 0.453(2) -0.0202(16) 0.091(8) Uiso 1 1 d D . . . .
H2O H 0.0715(12) 0.418(2) 0.3476(17) 0.067(7) Uiso 1 1 d 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
_geom_angle_publ_flag
C7 N1 C10 107.64(11) . . ?
C7 O3 C9 105.83(11) . . ?
N1 C7 O3 117.98(13) . . ?
N1 C7 C6 126.07(13) . . ?
O3 C7 C6 115.95(12) . . ?
N1 C10 C12 109.10(11) . . ?
N1 C10 C11 109.87(11) . . ?
C12 C10 C11 109.52(13) . . ?
N1 C10 C9 102.77(11) . . ?
C12 C10 C9 112.16(12) . . ?
C11 C10 C9 113.17(12) . . ?
C11 O2 H2O 110.2(16) . . ?
C5 C6 C1 118.87(15) . . ?
C5 C6 C7 121.26(14) . . ?
C1 C6 C7 119.86(14) . . ?
O3 C9 C10 104.76(11) . . ?
O3 C9 H9A 110.8 . . ?
C10 C9 H9A 110.8 . . ?
O3 C9 H9B 110.8 . . ?
C10 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
O2 C11 C10 112.87(13) . . ?
O2 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
O2 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O1 C12 C10 107.78(13) . . ?
O1 C12 H12A 110.1 . . ?
C10 C12 H12A 110.1 . . ?
O1 C12 H12B 110.1 . . ?
C10 C12 H12B 110.1 . . ?
H12A C12 H12B 108.5 . . ?
C12 O1 H1O 109.0(17) . . ?
C2 C1 C6 120.36(17) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C4 C5 C6 119.89(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C4 C3 C2 119.50(17) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C2 C1 120.48(18) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C3 C4 C5 120.90(19) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.2698(19) . ?
N1 C10 1.4796(17) . ?
O3 C7 1.3536(17) . ?
O3 C9 1.4449(18) . ?
C7 C6 1.470(2) . ?
C10 C12 1.521(2) . ?
C10 C11 1.525(2) . ?
C10 C9 1.540(2) . ?
O2 C11 1.4143(19) . ?
O2 H2O 0.854(16) . ?
C6 C5 1.388(2) . ?
C6 C1 1.389(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O1 1.414(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
O1 H1O 0.917(17) . ?
C1 C2 1.378(2) . ?
C1 H1 0.9300 . ?
C5 C4 1.384(3) . ?
C5 H5 0.9300 . ?
C3 C4 1.368(3) . ?
C3 C2 1.375(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{c3fb45ab-1843-4df9-9ca6-1c95715c8c35} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
?
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{c3fb45ab-1843-4df9-9ca6-1c95715c8c35} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
?

_cod_database_fobs_code 1559475
