Construction of Nitrated Benzo[3.3.1]bicyclic Acetal/Ketal Core via Nitration of o-Carbonyl Allylbenzenes.
Chan, Chieh-Kai; Tsai, Yu-Lin; Chang, Meng-Yang; Organic letters 19 (2017) 1358–1361; doi:10.1021/acs.orglett.7b00245

data_1545398
_publ_section_title
;
 Construction of Nitrated Benzo[3.3.1]bicyclic Acetal/Ketal Core via
 Nitration of o-Carbonyl Allylbenzenes.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1358
_journal_page_last               1361
_journal_paper_doi               10.1021/acs.orglett.7b00245
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C16 H12 O5'
_chemical_formula_weight         284.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 94.984(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4466(6)
_cell_length_b                   4.1414(2)
_cell_length_c                   29.0120(18)
_cell_measurement_reflns_used    1779
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.5388
_cell_measurement_theta_min      2.5092
_cell_volume                     1250.42(12)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7467
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.381
_diffrn_reflns_theta_min         1.409
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.7932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1078P)^2^+0.2773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.2068
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1440
_reflns_number_total             2474
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00245_si_009.cif
_cod_data_source_block           161044_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1545398--1545406.cif.
;
_cod_database_code               1545398
_shelxl_version_number           2014/6
_shelx_res_checksum              1446
_shelx_hkl_checksum              43219