#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/09/2230959.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_2230959
loop_
_publ_author_name
'Moumou, Mohamed'
'Benharref, Ahmed'
'Berraho, Moha'
'El Ammari, Lahcen'
'Akssira, Mohamed'
'Elhakmaoui, Ahmed'
_publ_section_title
;
 (Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-9(1aH)-one
;
_journal_coeditor_code           ZL2378
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1698
_journal_page_last               o1699
_journal_paper_doi               10.1107/S1600536811022616
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H29 N O5'
_chemical_formula_moiety         'C19 H29 N O5'
_chemical_formula_sum            'C19 H29 N O5'
_chemical_formula_weight         351.43
_chemical_name_systematic
;
(Z)-6-Hydroxy-1a,5-dimethyl-8-[(morpholin-4-yl)methyl]-
2,3,6,7,7a,8,10a,10b-octahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-
9(1aH)-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 101.328(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.7539(3)
_cell_length_b                   6.8304(2)
_cell_length_c                   11.8585(3)
_cell_measurement_reflns_used    11515
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      1.8
_cell_volume                     933.50(4)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11514
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.77
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         2086
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0327
_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)+(0.0640P)²+0.0786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0947
_reflns_number_gt                1987
_reflns_number_total             2086
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2378.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2230959
_cod_database_fobs_code          2230959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C4 0.68147(17) 0.6737(3) 0.7681(2) 0.0506(5) Uani d . 1 1 . .
H H4 0.7514 0.6984 0.8181 0.061 Uiso calc R 1 1 . .
C C1 0.59711(14) 0.3364(3) 0.86650(18) 0.0446(4) Uani d . 1 1 . .
C C2 0.56720(18) 0.5347(4) 0.9071(2) 0.0602(6) Uani d . 1 1 . .
H H2A 0.6204 0.5665 0.9782 0.072 Uiso calc R 1 1 . .
H H2B 0.4894 0.5311 0.9232 0.072 Uiso calc R 1 1 . .
C C3 0.5735(2) 0.6950(4) 0.8181(3) 0.0662(7) Uani d . 1 1 . .
H H3A 0.5056 0.6872 0.7569 0.079 Uiso calc R 1 1 . .
H H3B 0.5736 0.8224 0.8543 0.079 Uiso calc R 1 1 . .
C C5 0.68894(16) 0.6245(3) 0.66217(19) 0.0490(5) Uani d . 1 1 . .
C C6 0.80378(17) 0.5685(3) 0.63035(17) 0.0456(5) Uani d . 1 1 . .
H H6 0.7974 0.5963 0.5483 0.055 Uiso calc R 1 1 . .
C C7 0.82776(15) 0.3483(3) 0.64773(14) 0.0379(4) Uani d . 1 1 . .
H H7A 0.8859 0.3110 0.6039 0.045 Uiso calc R 1 1 . .
H H7B 0.7572 0.2775 0.6160 0.045 Uiso calc R 1 1 . .
C C8 0.86965(12) 0.2824(3) 0.77319(13) 0.0298(3) Uani d . 1 1 . .
H H8 0.8879 0.4000 0.8206 0.036 Uiso calc R 1 1 . .
C C11 0.97917(13) 0.1537(3) 0.79115(13) 0.0339(4) Uani d . 1 1 . .
H H11 0.9816 0.0817 0.7202 0.041 Uiso calc R 1 1 . .
C C12 0.96289(15) 0.0110(3) 0.88422(15) 0.0392(4) Uani d . 1 1 . .
C C9 0.78383(13) 0.1581(3) 0.82571(13) 0.0320(3) Uani d . 1 1 . .
H H9 0.7295 0.0892 0.7654 0.038 Uiso calc R 1 1 . .
C C10 0.71981(13) 0.2807(3) 0.89708(14) 0.0367(4) Uani d . 1 1 . .
H H10 0.7686 0.3785 0.9441 0.044 Uiso calc R 1 1 . .
C C14 0.5874(2) 0.6021(6) 0.5617(2) 0.0801(9) Uani d . 1 1 . .
H H14A 0.5162 0.6256 0.5876 0.120 Uiso calc R 1 1 . .
H H14B 0.5870 0.4718 0.5313 0.120 Uiso calc R 1 1 . .
H H14C 0.5950 0.6949 0.5028 0.120 Uiso calc R 1 1 . .
C C13 0.51592(17) 0.2541(4) 0.7628(2) 0.0627(6) Uani d . 1 1 . .
H H13A 0.5454 0.1310 0.7420 0.094 Uiso calc R 1 1 . .
H H13B 0.5101 0.3440 0.6997 0.094 Uiso calc R 1 1 . .
H H13C 0.4405 0.2349 0.7808 0.094 Uiso calc R 1 1 . .
C C15 1.09185(13) 0.2656(3) 0.82863(14) 0.0408(4) Uani d . 1 1 . .
H H15A 1.0922 0.3251 0.9030 0.049 Uiso calc R 1 1 . .
H H15B 1.1562 0.1742 0.8378 0.049 Uiso calc R 1 1 . .
C C16 1.14927(17) 0.3355(3) 0.64750(16) 0.0451(4) Uani d . 1 1 . .
H H16A 1.0909 0.2467 0.6069 0.054 Uiso calc R 1 1 . .
H H16B 1.2201 0.2617 0.6734 0.054 Uiso calc R 1 1 . .
C C17 1.1711(2) 0.4972(4) 0.5678(2) 0.0615(6) Uani d . 1 1 . .
H H17A 1.1966 0.4405 0.5019 0.074 Uiso calc R 1 1 . .
H H17B 1.0992 0.5669 0.5398 0.074 Uiso calc R 1 1 . .
C C19 1.19698(17) 0.5597(4) 0.80346(19) 0.0526(5) Uani d . 1 1 . .
H H19A 1.2686 0.4910 0.8339 0.063 Uiso calc R 1 1 . .
H H19B 1.1701 0.6210 0.8672 0.063 Uiso calc R 1 1 . .
C C18 1.2193(2) 0.7138(4) 0.7208(3) 0.0680(7) Uani d . 1 1 . .
H H18A 1.1490 0.7893 0.6953 0.082 Uiso calc R 1 1 . .
H H18B 1.2788 0.8022 0.7597 0.082 Uiso calc R 1 1 . .
N N 1.10962(11) 0.4195(3) 0.74672(12) 0.0387(4) Uani d . 1 1 . .
O O1 1.03350(12) -0.0969(3) 0.93835(13) 0.0577(4) Uani d . 1 1 . .
O O2 0.63581(11) 0.1901(3) 0.95455(13) 0.0552(4) Uani d . 1 1 . .
O O3 0.85411(10) 0.0191(2) 0.90318(10) 0.0397(3) Uani d . 1 1 . .
O O4 0.89640(12) 0.6831(3) 0.69114(15) 0.0587(4) Uani d . 1 1 . .
H H4A 0.9564 0.6187 0.7018 0.088 Uiso calc R 1 1 . .
O O5 1.25568(15) 0.6306(3) 0.62272(16) 0.0699(5) Uani d . 1 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
C5 C4 C3 . . 128.1(2) ?
C5 C4 H4 . . 116.0 ?
C3 C4 H4 . . 116.0 ?
O2 C1 C10 . . 59.33(11) ?
O2 C1 C2 . . 116.72(19) ?
C10 C1 C2 . . 115.79(19) ?
O2 C1 C13 . . 112.9(2) ?
C10 C1 C13 . . 122.61(19) ?
C2 C1 C13 . . 116.52(19) ?
C1 C2 C3 . . 112.15(19) ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2B . . 109.2 ?
C3 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C4 C3 C2 . . 111.12(19) ?
C4 C3 H3A . . 109.4 ?
C2 C3 H3A . . 109.4 ?
C4 C3 H3B . . 109.4 ?
C2 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C4 C5 C14 . . 125.7(2) ?
C4 C5 C6 . . 121.92(18) ?
C14 C5 C6 . . 112.3(2) ?
O4 C6 C5 . . 111.44(19) ?
O4 C6 C7 . . 111.71(16) ?
C5 C6 C7 . . 111.18(17) ?
O4 C6 H6 . . 107.4 ?
C5 C6 H6 . . 107.4 ?
C7 C6 H6 . . 107.4 ?
C6 C7 C8 . . 115.55(16) ?
C6 C7 H7A . . 108.4 ?
C8 C7 H7A . . 108.4 ?
C6 C7 H7B . . 108.4 ?
C8 C7 H7B . . 108.4 ?
H7A C7 H7B . . 107.5 ?
C11 C8 C7 . . 113.64(13) ?
C11 C8 C9 . . 103.05(13) ?
C7 C8 C9 . . 116.19(13) ?
C11 C8 H8 . . 107.9 ?
C7 C8 H8 . . 107.9 ?
C9 C8 H8 . . 107.9 ?
C12 C11 C15 . . 109.82(13) ?
C12 C11 C8 . . 104.29(12) ?
C15 C11 C8 . . 114.26(16) ?
C12 C11 H11 . . 109.4 ?
C15 C11 H11 . . 109.4 ?
C8 C11 H11 . . 109.4 ?
O1 C12 O3 . . 121.22(17) ?
O1 C12 C11 . . 127.88(16) ?
O3 C12 C11 . . 110.89(14) ?
O3 C9 C10 . . 107.07(13) ?
O3 C9 C8 . . 106.16(11) ?
C10 C9 C8 . . 111.28(15) ?
O3 C9 H9 . . 110.7 ?
C10 C9 H9 . . 110.7 ?
C8 C9 H9 . . 110.7 ?
O2 C10 C1 . . 59.83(12) ?
O2 C10 C9 . . 119.60(17) ?
C1 C10 C9 . . 125.82(16) ?
O2 C10 H10 . . 113.6 ?
C1 C10 H10 . . 113.6 ?
C9 C10 H10 . . 113.6 ?
C5 C14 H14A . . 109.5 ?
C5 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C5 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C1 C13 H13A . . 109.5 ?
C1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N C15 C11 . . 113.24(13) ?
N C15 H15A . . 108.9 ?
C11 C15 H15A . . 108.9 ?
N C15 H15B . . 108.9 ?
C11 C15 H15B . . 108.9 ?
H15A C15 H15B . . 107.7 ?
N C16 C17 . . 109.68(19) ?
N C16 H16A . . 109.7 ?
C17 C16 H16A . . 109.7 ?
N C16 H16B . . 109.7 ?
C17 C16 H16B . . 109.7 ?
H16A C16 H16B . . 108.2 ?
O5 C17 C16 . . 112.00(19) ?
O5 C17 H17A . . 109.2 ?
C16 C17 H17A . . 109.2 ?
O5 C17 H17B . . 109.2 ?
C16 C17 H17B . . 109.2 ?
H17A C17 H17B . . 107.9 ?
N C19 C18 . . 110.83(18) ?
N C19 H19A . . 109.5 ?
C18 C19 H19A . . 109.5 ?
N C19 H19B . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 108.1 ?
O5 C18 C19 . . 111.8(2) ?
O5 C18 H18A . . 109.3 ?
C19 C18 H18A . . 109.3 ?
O5 C18 H18B . . 109.3 ?
C19 C18 H18B . . 109.3 ?
H18A C18 H18B . . 107.9 ?
C16 N C19 . . 108.64(14) ?
C16 N C15 . . 111.03(17) ?
C19 N C15 . . 109.89(14) ?
C10 O2 C1 . . 60.83(11) ?
C12 O3 C9 . . 111.20(13) ?
C6 O4 H4A . . 109.5 ?
C17 O5 C18 . . 109.61(17) ?
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
C4 C5 . 1.320(3) ?
C4 C3 . 1.509(3) ?
C4 H4 . 0.9300 ?
C1 O2 . 1.452(3) ?
C1 C10 . 1.466(2) ?
C1 C2 . 1.503(4) ?
C1 C13 . 1.509(3) ?
C2 C3 . 1.533(4) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C5 C14 . 1.519(3) ?
C5 C6 . 1.520(3) ?
C6 O4 . 1.418(3) ?
C6 C7 . 1.537(3) ?
C6 H6 . 0.9800 ?
C7 C8 . 1.540(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C11 . 1.538(2) ?
C8 C9 . 1.540(2) ?
C8 H8 . 0.9800 ?
C11 C12 . 1.513(2) ?
C11 C15 . 1.518(2) ?
C11 H11 . 0.9800 ?
C12 O1 . 1.198(2) ?
C12 O3 . 1.342(2) ?
C9 O3 . 1.459(2) ?
C9 C10 . 1.495(2) ?
C9 H9 . 0.9800 ?
C10 O2 . 1.444(2) ?
C10 H10 . 0.9800 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C15 N . 1.473(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 N . 1.465(2) ?
C16 C17 . 1.509(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 O5 . 1.410(3) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C19 N . 1.467(3) ?
C19 C18 . 1.496(4) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C18 O5 . 1.433(3) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
O4 H4A . 0.8200 ?
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
O4 H4A N 1_555 0.82 2.24 3.051(2) 172 yes
C2 H2B O2 2_657 0.97 2.51 3.324(3) 142 yes
C10 H10 O1 2_757 0.98 2.47 3.270(2) 138 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656816
