Intermolecular CDC amination of remote and proximal unactivated Csp3–H bonds through intrinsic substrate reactivity – expanding towards a traceless directing group
Rajamanickam, Suresh; Saraswat, Mayank; Venkataramani, Sugumar; Patel, Bhisma K.; Chemical Science  (2021) –; doi:10.1039/D1SC04365J

data_1565264
_publ_section_title
;
 Intermolecular CDC amination of remote and proximal unactivated Csp3--H
 bonds through intrinsic substrate reactivity -- expanding towards a
 traceless directing group
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC04365J
_journal_year                    2021
_chemical_formula_moiety         'C19 H16 N6 O4'
_chemical_formula_sum            'C19 H16 N6 O4'
_chemical_formula_weight         392.38
_chemical_name_common            Organic
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-03-14 deposited with the CCDC.	2021-11-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6825(8)
_cell_length_b                   13.3272(13)
_cell_length_c                   18.012(2)
_cell_measurement_reflns_used    3504
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.422
_cell_measurement_theta_min      1.901
_cell_volume                     1844.2(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       'Omega and Phi Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20256
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.422
_diffrn_reflns_theta_min         1.901
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4435
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0455
_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^)+0.1183P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.890
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                2574
_reflns_number_total             4435
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc04365j2.cif
_cod_data_source_block           RSH_30012021
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1565264
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              53246