#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151845.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_7151845
loop_
_publ_author_name
'Bondalapati, Somasekhar'
'Reddy, Udagandla C.'
'Saha, Pipas'
'Saikia, Anil K.'
_publ_section_title
;
 An efficient synthesis of dihydro- and tetrahydropyrans via
 oxonium-ene cyclization reaction.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3428
_journal_page_last               3438
_journal_paper_doi               10.1039/c1ob00033k
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C19 H20 N2 O4'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.451(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.6207(12)
_cell_length_b                   19.274(2)
_cell_length_c                   16.3163(15)
_cell_measurement_reflns_used    1395
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      13.12
_cell_measurement_theta_min      2.37
_cell_volume                     3593.9(6)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0857
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17415
_diffrn_reflns_theta_full        27.77
_diffrn_reflns_theta_max         27.77
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         8475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0522
_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)+(0.0768P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1411
_reflns_number_gt                6487
_reflns_number_total             8475
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob00033k.txt
_cod_data_source_block           somu-231
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        3593.8(6)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7151845
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0283(6) 0.3607(4) 0.9258(4) 0.078(2) Uani 1 1 d . . .
H1A H -0.0528 0.3259 0.9620 0.093 Uiso 1 1 calc R . .
H1B H 0.0543 0.3697 0.9453 0.093 Uiso 1 1 calc R . .
C2 C -0.0453(5) 0.3327(3) 0.8384(5) 0.072(2) Uani 1 1 d . . .
H2A H -0.1267 0.3199 0.8204 0.087 Uiso 1 1 calc R . .
H2B H 0.0019 0.2913 0.8376 0.087 Uiso 1 1 calc R . .
C3 C -0.0110(7) 0.3860(3) 0.7777(4) 0.0574(17) Uani 1 1 d . . .
C4 C -0.0778(5) 0.4531(3) 0.7900(4) 0.0607(18) Uani 1 1 d . . .
H4A H -0.0519 0.4898 0.7569 0.073 Uiso 1 1 calc R . .
H4B H -0.1607 0.4458 0.7698 0.073 Uiso 1 1 calc R . .
C5 C -0.0593(5) 0.4759(4) 0.8808(4) 0.0565(18) Uani 1 1 d . . .
H5 H 0.0240 0.4858 0.8995 0.068 Uiso 1 1 calc R . .
C6 C -0.1279(7) 0.5403(5) 0.8928(5) 0.0541(18) Uani 1 1 d . . .
C7 C -0.2173(8) 0.5425(4) 0.9382(4) 0.068(2) Uani 1 1 d . . .
H7 H -0.2357 0.5030 0.9659 0.081 Uiso 1 1 calc R . .
C8 C -0.2802(6) 0.6038(6) 0.9426(4) 0.075(2) Uani 1 1 d . . .
H8 H -0.3421 0.6044 0.9717 0.090 Uiso 1 1 calc R . .
C9 C -0.2512(8) 0.6629(4) 0.9044(5) 0.074(2) Uani 1 1 d . . .
H9 H -0.2913 0.7042 0.9081 0.089 Uiso 1 1 calc R . .
C10 C -0.1607(8) 0.6594(6) 0.8604(4) 0.067(2) Uani 1 1 d . . .
C11 C -0.1004(6) 0.5995(6) 0.8534(4) 0.064(2) Uani 1 1 d . . .
H11 H -0.0410 0.5988 0.8221 0.077 Uiso 1 1 calc R . .
C12 C -0.0424(5) 0.3615(3) 0.6872(4) 0.087(2) Uani 1 1 d . . .
H12A H -0.0239 0.3973 0.6508 0.131 Uiso 1 1 calc R . .
H12B H -0.1246 0.3513 0.6740 0.131 Uiso 1 1 calc R . .
H12C H 0.0015 0.3205 0.6800 0.131 Uiso 1 1 calc R . .
C13 C 0.2040(8) 0.3567(5) 0.8047(3) 0.0571(19) Uani 1 1 d . . .
C14 C 0.3234(8) 0.3886(5) 0.8160(4) 0.0529(18) Uani 1 1 d . . .
C15 C 0.3503(9) 0.4540(6) 0.8473(4) 0.069(2) Uani 1 1 d . . .
H15 H 0.2931 0.4805 0.8658 0.083 Uiso 1 1 calc R . .
C16 C 0.4609(12) 0.4808(4) 0.8516(5) 0.087(2) Uani 1 1 d . . .
H16 H 0.4785 0.5247 0.8741 0.105 Uiso 1 1 calc R . .
C17 C 0.5455(7) 0.4428(6) 0.8228(5) 0.083(2) Uani 1 1 d . . .
H17 H 0.6194 0.4617 0.8237 0.100 Uiso 1 1 calc R . .
C18 C 0.5208(10) 0.3769(6) 0.7928(4) 0.084(2) Uani 1 1 d . . .
H18 H 0.5782 0.3507 0.7744 0.100 Uiso 1 1 calc R . .
C19 C 0.4111(11) 0.3500(4) 0.7901(4) 0.070(2) Uani 1 1 d . . .
H19 H 0.3951 0.3051 0.7706 0.084 Uiso 1 1 calc R . .
C20 C 0.3118(8) 0.6685(4) 0.5426(4) 0.093(2) Uani 1 1 d . . .
H20A H 0.3366 0.7013 0.5041 0.111 Uiso 1 1 calc R . .
H20B H 0.3602 0.6756 0.5970 0.111 Uiso 1 1 calc R . .
C21 C 0.1848(7) 0.6820(3) 0.5480(4) 0.085(2) Uani 1 1 d . . .
H21A H 0.1372 0.6779 0.4929 0.102 Uiso 1 1 calc R . .
H21B H 0.1770 0.7290 0.5675 0.102 Uiso 1 1 calc R . .
C22 C 0.1399(7) 0.6313(4) 0.6068(5) 0.0651(19) Uani 1 1 d . . .
C23 C 0.1720(7) 0.5577(4) 0.5817(4) 0.077(2) Uani 1 1 d . . .
H23A H 0.1565 0.5252 0.6238 0.092 Uiso 1 1 calc R . .
H23B H 0.1216 0.5454 0.5296 0.092 Uiso 1 1 calc R . .
C24 C 0.2964(8) 0.5500(4) 0.5716(5) 0.081(2) Uani 1 1 d . . .
H24 H 0.3472 0.5559 0.6261 0.098 Uiso 1 1 calc R . .
C25 C 0.3173(6) 0.4788(5) 0.5378(8) 0.088(2) Uani 1 1 d . . .
C26 C 0.3191(9) 0.4214(8) 0.5870(6) 0.157(4) Uani 1 1 d . . .
H26 H 0.3117 0.4274 0.6424 0.189 Uiso 1 1 calc R . .
C27 C 0.3314(10) 0.3546(7) 0.5586(9) 0.179(5) Uani 1 1 d . . .
H27 H 0.3296 0.3169 0.5939 0.214 Uiso 1 1 calc R . .
C28 C 0.3460(8) 0.3447(5) 0.4790(10) 0.135(4) Uani 1 1 d . . .
H28 H 0.3559 0.3006 0.4583 0.161 Uiso 1 1 calc R . .
C29 C 0.3457(6) 0.4027(8) 0.4302(6) 0.092(3) Uani 1 1 d . . .
C30 C 0.3305(6) 0.4690(5) 0.4572(8) 0.089(3) Uani 1 1 d . . .
H30 H 0.3292 0.5066 0.4212 0.106 Uiso 1 1 calc R . .
C31 C 0.0082(6) 0.6375(3) 0.6024(4) 0.096(2) Uani 1 1 d . . .
H31A H -0.0166 0.6045 0.6398 0.144 Uiso 1 1 calc R . .
H31B H -0.0313 0.6282 0.5465 0.144 Uiso 1 1 calc R . .
H31C H -0.0105 0.6835 0.6182 0.144 Uiso 1 1 calc R . .
C32 C 0.1961(6) 0.6121(4) 0.7622(5) 0.0543(19) Uani 1 1 d . . .
C33 C 0.2684(8) 0.6393(4) 0.8400(5) 0.0498(17) Uani 1 1 d . . .
C34 C 0.3700(9) 0.6769(4) 0.8408(5) 0.065(2) Uani 1 1 d . . .
H34 H 0.3940 0.6874 0.7909 0.079 Uiso 1 1 calc R . .
C35 C 0.4361(6) 0.6991(3) 0.9152(8) 0.078(2) Uani 1 1 d . . .
H35 H 0.5042 0.7244 0.9149 0.093 Uiso 1 1 calc R . .
C36 C 0.4017(9) 0.6840(4) 0.9901(5) 0.080(2) Uani 1 1 d . . .
H36 H 0.4467 0.6982 1.0404 0.095 Uiso 1 1 calc R . .
C37 C 0.2992(9) 0.6474(4) 0.9888(6) 0.079(2) Uani 1 1 d . . .
H37 H 0.2737 0.6378 1.0385 0.094 Uiso 1 1 calc R . .
C38 C 0.2359(6) 0.6255(3) 0.9158(7) 0.065(2) Uani 1 1 d . . .
H38 H 0.1679 0.6002 0.9165 0.078 Uiso 1 1 calc R . .
N1 N 0.1153(6) 0.4028(3) 0.7975(3) 0.0593(15) Uani 1 1 d . . .
H1 H 0.1339 0.4459 0.8050 0.071 Uiso 1 1 calc R . .
N2 N -0.1323(7) 0.7230(4) 0.8208(5) 0.108(2) Uani 1 1 d . . .
N3 N 0.2011(4) 0.6475(2) 0.6919(4) 0.0579(15) Uani 1 1 d . . .
H3 H 0.2451 0.6838 0.6972 0.069 Uiso 1 1 calc R . .
N4 N 0.3629(7) 0.3932(4) 0.3433(6) 0.127(3) Uani 1 1 d . . .
O1 O -0.0926(4) 0.4232(3) 0.9318(3) 0.0710(13) Uani 1 1 d . . .
O2 O 0.1898(4) 0.2934(3) 0.8035(3) 0.0769(16) Uani 1 1 d . . .
O3 O -0.1858(5) 0.7762(3) 0.8281(3) 0.118(2) Uani 1 1 d . . .
O4 O -0.0513(7) 0.7213(3) 0.7843(4) 0.179(4) Uani 1 1 d . . .
O5 O 0.3279(4) 0.5998(3) 0.5152(3) 0.0971(16) Uani 1 1 d . . .
O6 O 0.1361(4) 0.5591(2) 0.7626(3) 0.0660(14) Uani 1 1 d . . .
O7 O 0.3803(7) 0.3360(4) 0.3195(4) 0.180(3) Uani 1 1 d . . .
O8 O 0.3546(7) 0.4417(4) 0.2980(4) 0.183(3) 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
_geom_angle_publ_flag
O1 C1 C2 112.8(5) . . ?
C1 C2 C3 111.6(5) . . ?
N1 C3 C2 111.8(5) . . ?
N1 C3 C12 109.4(5) . . ?
C2 C3 C12 111.9(6) . . ?
N1 C3 C4 106.9(6) . . ?
C2 C3 C4 106.5(5) . . ?
C12 C3 C4 110.3(6) . . ?
C5 C4 C3 112.6(5) . . ?
O1 C5 C6 108.0(6) . . ?
O1 C5 C4 111.1(5) . . ?
C6 C5 C4 112.4(6) . . ?
C11 C6 C7 119.1(6) . . ?
C11 C6 C5 116.7(9) . . ?
C7 C6 C5 124.1(9) . . ?
C6 C7 C8 120.3(6) . . ?
C9 C8 C7 120.3(7) . . ?
C8 C9 C10 118.0(7) . . ?
C11 C10 C9 122.5(8) . . ?
C11 C10 N2 121.0(9) . . ?
C9 C10 N2 116.5(10) . . ?
C10 C11 C6 119.7(7) . . ?
O2 C13 N1 123.6(7) . . ?
O2 C13 C14 121.8(8) . . ?
N1 C13 C14 114.5(7) . . ?
C15 C14 C19 118.3(7) . . ?
C15 C14 C13 124.4(9) . . ?
C19 C14 C13 117.2(10) . . ?
C16 C15 C14 120.7(7) . . ?
C15 C16 C17 120.2(7) . . ?
C18 C17 C16 119.9(8) . . ?
C19 C18 C17 119.7(7) . . ?
C18 C19 C14 121.2(7) . . ?
O5 C20 C21 111.3(6) . . ?
C20 C21 C22 112.0(6) . . ?
N3 C22 C31 109.7(6) . . ?
N3 C22 C21 107.2(6) . . ?
C31 C22 C21 112.1(6) . . ?
N3 C22 C23 110.3(5) . . ?
C31 C22 C23 110.3(6) . . ?
C21 C22 C23 107.2(6) . . ?
C24 C23 C22 114.0(6) . . ?
O5 C24 C23 111.9(6) . . ?
O5 C24 C25 107.3(7) . . ?
C23 C24 C25 110.6(7) . . ?
C30 C25 C26 117.6(8) . . ?
C30 C25 C24 121.9(10) . . ?
C26 C25 C24 120.4(11) . . ?
C25 C26 C27 123.2(9) . . ?
C28 C27 C26 119.4(9) . . ?
C27 C28 C29 117.1(9) . . ?
C28 C29 C30 123.9(8) . . ?
C28 C29 N4 118.0(12) . . ?
C30 C29 N4 118.1(12) . . ?
C25 C30 C29 118.7(8) . . ?
O6 C32 N3 122.4(7) . . ?
O6 C32 C33 121.2(7) . . ?
N3 C32 C33 116.4(7) . . ?
C38 C33 C34 117.6(7) . . ?
C38 C33 C32 119.5(9) . . ?
C34 C33 C32 122.9(9) . . ?
C35 C34 C33 120.6(7) . . ?
C34 C35 C36 120.5(7) . . ?
C37 C36 C35 118.7(7) . . ?
C38 C37 C36 120.3(7) . . ?
C37 C38 C33 122.3(7) . . ?
C13 N1 C3 125.8(6) . . ?
O4 N2 O3 122.0(8) . . ?
O4 N2 C10 117.4(8) . . ?
O3 N2 C10 120.6(8) . . ?
C32 N3 C22 127.4(6) . . ?
O8 N4 O7 121.5(10) . . ?
O8 N4 C29 119.3(10) . . ?
O7 N4 C29 119.1(9) . . ?
C5 O1 C1 111.3(5) . . ?
C20 O5 C24 111.1(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
C1 O1 1.430(6) . ?
C1 C2 1.504(7) . ?
C2 C3 1.528(7) . ?
C3 N1 1.481(7) . ?
C3 C12 1.530(7) . ?
C3 C4 1.540(7) . ?
C4 C5 1.523(7) . ?
C5 O1 1.412(6) . ?
C5 C6 1.507(7) . ?
C6 C11 1.375(7) . ?
C6 C7 1.382(8) . ?
C7 C8 1.398(8) . ?
C8 C9 1.371(8) . ?
C9 C10 1.378(8) . ?
C10 C11 1.365(8) . ?
C10 N2 1.451(9) . ?
C13 O2 1.229(7) . ?
C13 N1 1.351(7) . ?
C13 C14 1.498(9) . ?
C14 C15 1.376(8) . ?
C14 C19 1.388(8) . ?
C16 C17 1.375(8) . ?
C17 C18 1.373(8) . ?
C20 O5 1.421(6) . ?
C20 C21 1.517(8) . ?
C21 C22 1.526(8) . ?
C22 N3 1.474(7) . ?
C22 C31 1.524(7) . ?
C22 C23 1.542(7) . ?
C23 C24 1.492(8) . ?
C24 O5 1.424(7) . ?
C24 C25 1.515(9) . ?
C25 C26 1.365(9) . ?
C26 C27 1.384(10) . ?
C27 C28 1.353(10) . ?
C28 C29 1.372(10) . ?
C29 C30 1.375(9) . ?
C29 N4 1.478(10) . ?
C32 O6 1.238(7) . ?
C32 N3 1.345(7) . ?
C32 C33 1.486(8) . ?
C33 C38 1.383(7) . ?
C33 C34 1.384(8) . ?
C34 C35 1.381(7) . ?
C35 C36 1.385(8) . ?
C36 C37 1.382(8) . ?
C37 C38 1.349(7) . ?
N2 O4 1.203(6) . ?
N2 O3 1.216(6) . ?
N4 O8 1.185(7) . ?
N4 O7 1.197(7) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190657
