(3 + 3) Annulation of Nitroallylic Acetates with Stabilized Sulfur Ylides for the Synthesis of 2-Aryl Terephthalates.
Satham, Lakshminarayana; Namboothiri, Irishi N. N.; The Journal of organic chemistry 83 (2018) 9471–9477; doi:10.1021/acs.joc.8b00917

data_4035303
_publ_section_title
;
 (3 + 3) Annulation of Nitroallylic Acetates with Stabilized Sulfur Ylides
 for the Synthesis of 2-Aryl Terephthalates.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9471
_journal_page_last               9477
_journal_paper_doi               10.1021/acs.joc.8b00917
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H15 N O6'
_chemical_formula_sum            'C17 H15 N O6'
_chemical_formula_weight         329.30
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                107.095(2)
_cell_angle_beta                 99.206(2)
_cell_angle_gamma                98.222(2)
_cell_formula_units_Z            8
_cell_length_a                   9.6495(3)
_cell_length_b                   15.4042(4)
_cell_length_c                   22.5104(6)
_cell_measurement_reflns_used    14940
_cell_measurement_temperature    150
_cell_measurement_theta_max      31.0900
_cell_measurement_theta_min      2.0460
_cell_volume                     3092.28(16)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.8903
_diffrn_measured_fraction_theta_max 0.8904
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -110.00  16.00   0.50    8.00    --  -20.00   0.00  36.00  252
  2  \w   -110.00  10.00   0.50    8.00    --  -20.00 -72.00  36.00  240
  3  \w    -81.00  19.00   0.50    8.00    --  -20.00 -72.00-180.00  200
  4  \w    -41.00  -2.00   0.50    8.00    --  -20.00  72.00 -36.00   78
  5  \w    -59.00 -28.50   0.50    8.00    --  -20.00  72.00-180.00   61
  6  \w    -22.00   9.00   0.50    8.00    --  -20.00 -72.00-108.00   62
  7  \w   -110.00  70.00   0.50    8.00    --  -20.00   0.00 -36.00  360
  8  \w    -87.00  -5.50   0.50    8.00    --  -20.00 -72.00 -36.00  163
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku saturn 724+'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0321087000
_diffrn_orient_matrix_UB_12      0.0460879000
_diffrn_orient_matrix_UB_13      0.0034395000
_diffrn_orient_matrix_UB_21      0.0101464000
_diffrn_orient_matrix_UB_22      -0.0149555000
_diffrn_orient_matrix_UB_23      -0.0316696000
_diffrn_orient_matrix_UB_31      -0.0681591000
_diffrn_orient_matrix_UB_32      0.0084353000
_diffrn_orient_matrix_UB_33      -0.0111323000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41061
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.183
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       needle
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     873
_refine_ls_number_reflns         10826
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1040P)^2^+0.2010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1930
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6359
_reflns_number_total             10826
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00917_si_002.cif
_cod_data_source_block           inn-sln-ii-178-a_mo
_cod_database_code               4035303
_chemical_oxdiff_formula         C19O5
_reflns_odcompleteness_completeness 89.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.14
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C48(H48A,H48B), C52(H52A,H52B), C51(H51A,H51B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C13(H13), C19(H19), C29(H29), C30(H30), C32(H32), C34(H34), C8(H8),
 C18(H18), C22(H22), C24(H24), C28(H28), C31(H31), C44(H44), C5(H5), C15(H15),
 C16(H16), C27(H27), C38(H38), C49(H49), C56(H56), C1(H1), C20(H20), C21(H21),
 C23(H23), C25(H25), C26(H26), C40(H40)
2.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C64(H64A,H64B,
 H64C), C58(H58A,H58B,H58C), C63(H63A,H63B,H63C), C35(H35A,H35B,H35C), C62(H62A,
 H62B,H62C)
;
_shelx_res_checksum              10309
_shelx_hkl_checksum              70710
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.749