Co-Catalyzed Highly Selective C(sp3)−H Nitration
Zhou, Yao; Tang, Zhonghe; Song, Qiuling; Chem. Commun.  (2017) –; doi:10.1039/C7CC04433J

data_7120410
_publ_section_title
;
 Co-Catalyzed Highly Selective C(sp3)&#x2212;H Nitration
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC04433J
_journal_year                    2017
_chemical_compound_source        NO
_chemical_formula_moiety         'C13 H13 N3 O2'
_chemical_formula_sum            'C13 H13 N3 O2'
_chemical_formula_weight         243.26
_chemical_melting_point          Unaware
_chemical_name_common            No
_chemical_name_systematic        4-(2-nitropropan-2-yl)-2-phenylpyrimidine
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc1n7jfv
_audit_creation_date             2016-11-18
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2017-01-10 deposited with the CCDC.
2017-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                89.395(10)
_cell_angle_beta                 88.058(10)
_cell_angle_gamma                89.171(10)
_cell_formula_units_Z            4
_cell_length_a                   7.3577(9)
_cell_length_b                   9.9881(11)
_cell_length_c                   16.612(2)
_cell_measurement_reflns_used    1377
_cell_measurement_temperature    295.28(10)
_cell_measurement_theta_max      27.4420
_cell_measurement_theta_min      3.4590
_cell_volume                     1219.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.28(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.807
_diffrn_measured_fraction_theta_max 0.661
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0014551000
_diffrn_orient_matrix_UB_12      -0.0670642000
_diffrn_orient_matrix_UB_13      0.0144639000
_diffrn_orient_matrix_UB_21      0.0201969000
_diffrn_orient_matrix_UB_22      -0.0228700000
_diffrn_orient_matrix_UB_23      -0.0396254000
_diffrn_orient_matrix_UB_31      0.0943211000
_diffrn_orient_matrix_UB_32      0.0048961000
_diffrn_orient_matrix_UB_33      0.0067798000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.807
_diffrn_reflns_Laue_measured_fraction_max 0.661
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5677
_diffrn_reflns_point_group_measured_fraction_full 0.807
_diffrn_reflns_point_group_measured_fraction_max 0.661
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.106
_diffrn_reflns_theta_min         2.992
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4325
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1379
_refine_ls_R_factor_gt           0.0862
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1235P)^2^+0.5731P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2414
_refine_ls_wR_factor_ref         0.2856
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2451
_reflns_number_total             4325
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc04433j2.cif
_cod_data_source_block           exp_3037
_cod_original_cell_volume        1219.9(3)
_cod_database_code               7120410
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 79.24
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23),
 C24(H24), C26(H26), C28(H28), C30(H30), C31(H31), C33(H33)
2.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C)
;
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.594
_oxdiff_exptl_absorpt_empirical_full_min 0.635