A Free Radical Nitration of Olefins with NaNO2/I2O5
Huang, Xuan; You, Huichao; Fang, Fang; Wang, Fan; Liu, Zhongquan; Chemical Communications  (2023) –; doi:10.1039/D3CC04275H

data_7132226
_publ_section_title
;
 A Free Radical Nitration of Olefins with NaNO2/I2O5
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04275H
_journal_year                    2023
_chemical_formula_moiety         'C12 H10 N2 O4'
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-10
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
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_audit_update_record
;
2023-07-11 deposited with the CCDC.	2023-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.888(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5350(6)
_cell_length_b                   14.4032(11)
_cell_length_c                   10.8824(8)
_cell_measurement_reflns_used    661
_cell_measurement_temperature    292.61(10)
_cell_measurement_theta_max      22.1570
_cell_measurement_theta_min      3.8240
_cell_volume                     1155.72(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.61(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega -102.00  -63.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000   60.0000 26

  2 omega    9.00   67.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000  -30.0000 39

  3 omega  -33.00   82.50   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867    0.0000  -30.0000 77
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0817822000
_diffrn_orient_matrix_UB_12      0.0193000000
_diffrn_orient_matrix_UB_13      0.0111440000
_diffrn_orient_matrix_UB_21      -0.0358220000
_diffrn_orient_matrix_UB_22      -0.0453035000
_diffrn_orient_matrix_UB_23      0.0031068000
_diffrn_orient_matrix_UB_31      0.0357553000
_diffrn_orient_matrix_UB_32      -0.0011397000
_diffrn_orient_matrix_UB_33      0.0656024000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            3963
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.334
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0612P)^2^+0.3620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1772
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1280
_reflns_number_total             2271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04275h2.cif
_cod_data_source_block           zhangyy_0507
_cod_original_cell_volume        1155.71(16)
_cod_database_code               7132226
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12)
;
_olex2_date_sample_data_collection 2017-05-09
_olex2_submission_special_instructions 'No special instructions were received'