#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151708.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_7151708
loop_
_publ_author_name
'Hong, Bor-Cherng'
'Kotame, Prakash'
'Liao, Ju-Hsiou'
_publ_section_title
;
 Enantioselective organocatalytic domino Michael-acetalization-Henry
 reactions of 2-hydroxynitrostyrene and aldehyde for the synthesis of
 tetrahydro-6H-benzo[c]chromenones.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              382
_journal_page_last               386
_journal_paper_doi               10.1039/C0OB00834F
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_formula_sum            'C12 H13 N O4'
_chemical_formula_weight         235.23
_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                 99.649(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.6540(9)
_cell_length_b                   7.4586(12)
_cell_length_c                   13.100(2)
_cell_measurement_reflns_used    586
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.529
_cell_measurement_theta_min      -23.529
_cell_volume                     544.62(15)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    Ortep-3
_computing_publication_material  'Wingx publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex'
_diffrn_measurement_method       'phi-omega scan'
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5325
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.58
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9929
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1960
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0369
_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)+(0.0446P)²+0.0563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0881
_reflns_number_gt                1759
_reflns_number_total             1960
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00834F.TXT
_cod_data_source_block           pmk0223
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical'
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_sg_symbol_H-M      'P 21'
_cod_database_code               7151708
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4710(3) 0.7116(2) 0.13997(11) 0.0195(4) Uani 1 1 d . . .
O2 O 0.6099(3) 0.9757(2) 0.19217(12) 0.0234(4) Uani 1 1 d . . .
O3 O 0.6371(3) 0.6838(3) 0.37246(14) 0.0361(5) Uani 1 1 d . . .
O4 O 0.5219(3) 0.4232(2) 0.41492(14) 0.0381(5) Uani 1 1 d . . .
N1 N 0.4827(4) 0.5806(3) 0.39161(14) 0.0216(4) Uani 1 1 d . . .
C1 C 0.1235(4) 0.5779(3) 0.19827(15) 0.0154(5) Uani 1 1 d . . .
C2 C -0.0463(4) 0.4409(3) 0.18495(17) 0.0179(5) Uani 1 1 d . . .
H2 H -0.1671 0.4380 0.2273 0.021 Uiso 1 1 calc R . .
C3 C -0.0420(4) 0.3085(3) 0.11078(17) 0.0204(5) Uani 1 1 d . . .
H3 H -0.1595 0.2163 0.1024 0.025 Uiso 1 1 calc R . .
C4 C 0.1345(4) 0.3113(3) 0.04891(17) 0.0206(5) Uani 1 1 d . . .
H4 H 0.1393 0.2199 -0.0012 0.025 Uiso 1 1 calc R . .
C5 C 0.3040(4) 0.4473(3) 0.06025(17) 0.0195(5) Uani 1 1 d . . .
H5 H 0.4249 0.4504 0.0179 0.023 Uiso 1 1 calc R . .
C6 C 0.2945(4) 0.5783(3) 0.13387(17) 0.0173(5) Uani 1 1 d . . .
C7 C 0.4522(4) 0.8683(3) 0.19313(17) 0.0182(5) Uani 1 1 d . . .
C8 C 0.2326(4) 0.8969(3) 0.24235(17) 0.0159(5) Uani 1 1 d . . .
H8 H 0.1070 0.9444 0.1859 0.019 Uiso 1 1 calc R . .
C9 C 0.1272(4) 0.7220(3) 0.27916(16) 0.0164(5) Uani 1 1 d . . .
H9 H -0.0448 0.7488 0.2822 0.020 Uiso 1 1 calc R . .
C10 C 0.2354(4) 0.6520(3) 0.38676(17) 0.0175(5) Uani 1 1 d . . .
H10A H 0.2386 0.7505 0.4376 0.021 Uiso 1 1 calc R . .
H10B H 0.1312 0.5558 0.4066 0.021 Uiso 1 1 calc R . .
C11 C 0.2777(4) 1.0468(3) 0.32295(17) 0.0191(5) Uani 1 1 d . . .
H11A H 0.4125 1.0110 0.3775 0.023 Uiso 1 1 calc R . .
H11B H 0.3272 1.1561 0.2892 0.023 Uiso 1 1 calc R . .
C12 C 0.0616(4) 1.0920(3) 0.37381(18) 0.0227(5) Uani 1 1 d . . .
H12A H 0.0204 0.9881 0.4131 0.034 Uiso 1 1 calc R . .
H12B H -0.0752 1.1229 0.3203 0.034 Uiso 1 1 calc R . .
H12C H 0.1005 1.1941 0.4207 0.034 Uiso 1 1 calc R . .
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 O1 C6 121.18(17) . . ?
O3 N1 O4 123.4(2) . . ?
O3 N1 C10 117.69(19) . . ?
O4 N1 C10 118.9(2) . . ?
C6 C1 C2 117.5(2) . . ?
C6 C1 C9 119.83(19) . . ?
C2 C1 C9 122.63(19) . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 119.1(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 122.4(2) . . ?
C5 C6 O1 115.57(19) . . ?
C1 C6 O1 122.0(2) . . ?
O2 C7 O1 116.21(19) . . ?
O2 C7 C8 125.2(2) . . ?
O1 C7 C8 118.45(18) . . ?
C7 C8 C11 110.16(18) . . ?
C7 C8 C9 113.76(17) . . ?
C11 C8 C9 115.48(17) . . ?
C7 C8 H8 105.5 . . ?
C11 C8 H8 105.5 . . ?
C9 C8 H8 105.5 . . ?
C1 C9 C10 111.12(18) . . ?
C1 C9 C8 110.09(17) . . ?
C10 C9 C8 117.38(18) . . ?
C1 C9 H9 105.8 . . ?
C10 C9 H9 105.8 . . ?
C8 C9 H9 105.8 . . ?
N1 C10 C9 112.89(17) . . ?
N1 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
N1 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C8 114.23(19) . . ?
C12 C11 H11A 108.7 . . ?
C8 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C8 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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
O1 C7 1.374(3) . ?
O1 C6 1.401(3) . ?
O2 C7 1.200(3) . ?
O3 N1 1.221(3) . ?
O4 N1 1.224(3) . ?
N1 C10 1.488(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.393(3) . ?
C1 C9 1.507(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.507(3) . ?
C8 C11 1.529(3) . ?
C8 C9 1.545(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.531(3) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.524(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28418553
2 PubChem 49817746
