#------------------------------------------------------------------------------
#$Date: 2021-11-17 01:19:28 +0200 (Wed, 17 Nov 2021) $
#$Revision: 270701 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/52/1565264.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1565264
loop_
_publ_author_name
'Rajamanickam, Suresh'
'Saraswat, Mayank'
'Venkataramani, Sugumar'
'Patel, Bhisma K.'
_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/[σ²(Fo²)+0.1183P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4108(4) 0.01553(19) 0.61617(15) 0.0783(8) Uani 1 1 d . . . . .
O2 O 0.3294(4) 0.32994(19) 0.52654(15) 0.0723(8) Uani 1 1 d . . . . .
O3 O -0.0387(5) 0.1125(3) -0.06218(19) 0.1033(11) Uani 1 1 d . . . . .
O4 O -0.0541(5) 0.2735(3) -0.06084(17) 0.0975(11) Uani 1 1 d . . . . .
N1 N 0.3649(4) 0.1624(2) 0.55228(14) 0.0535(7) Uani 1 1 d . . . . .
N2 N 0.3838(4) 0.1189(2) 0.28237(16) 0.0556(7) Uani 1 1 d . . . . .
N3 N 0.4603(4) 0.1592(2) 0.34075(16) 0.0545(7) Uani 1 1 d . . . . .
N4 N 0.4663(5) 0.2579(2) 0.33975(19) 0.0666(9) Uani 1 1 d . . . . .
N5 N 0.3889(5) 0.2852(2) 0.27769(19) 0.0681(9) Uani 1 1 d . . . . .
N6 N -0.0085(5) 0.1933(3) -0.03327(19) 0.0744(10) Uani 1 1 d . . . . .
C1 C 0.4256(5) 0.1052(3) 0.6116(2) 0.0565(9) Uani 1 1 d . . . . .
C2 C 0.5002(5) 0.1764(3) 0.66516(18) 0.0552(9) Uani 1 1 d . . . . .
C3 C 0.5797(5) 0.1597(3) 0.7321(2) 0.0665(10) Uani 1 1 d . . . . .
H3 H 0.598670 0.094929 0.749487 0.080 Uiso 1 1 calc R U . . .
C4 C 0.6303(6) 0.2418(4) 0.7725(2) 0.0804(13) Uani 1 1 d . . . . .
H4 H 0.685561 0.232767 0.817940 0.097 Uiso 1 1 calc R U . . .
C5 C 0.6005(6) 0.3370(4) 0.7466(3) 0.0805(13) Uani 1 1 d . . . . .
H5 H 0.634142 0.391443 0.775611 0.097 Uiso 1 1 calc R U . . .
C6 C 0.5214(5) 0.3547(3) 0.6785(2) 0.0696(11) Uani 1 1 d . . . . .
H6 H 0.502253 0.419370 0.660883 0.084 Uiso 1 1 calc R U . . .
C7 C 0.4731(4) 0.2716(3) 0.6385(2) 0.0525(8) Uani 1 1 d . . . . .
C8 C 0.3820(4) 0.2638(3) 0.5661(2) 0.0534(9) Uani 1 1 d . . . . .
C9 C 0.2724(5) 0.1187(3) 0.48896(19) 0.0620(10) Uani 1 1 d . . . . .
H9A H 0.230303 0.172320 0.457269 0.074 Uiso 1 1 calc R U . . .
H9AB H 0.172113 0.081747 0.506960 0.074 Uiso 1 1 calc R U . . .
C10 C 0.3864(5) 0.0488(3) 0.4435(2) 0.0627(10) Uani 1 1 d . . . . .
H10A H 0.435803 -0.001198 0.476466 0.075 Uiso 1 1 calc R U . . .
H10B H 0.313469 0.013914 0.407923 0.075 Uiso 1 1 calc R U . . .
C11 C 0.5327(5) 0.0993(3) 0.40208(19) 0.0571(9) Uani 1 1 d . . . . .
H11 H 0.592557 0.144807 0.436355 0.069 Uiso 1 1 calc R U . . .
C12 C 0.6649(6) 0.0249(3) 0.3722(2) 0.0717(11) Uani 1 1 d . . . . .
H12A H 0.606753 -0.023875 0.341814 0.108 Uiso 1 1 calc R U . . .
H12B H 0.721299 -0.008387 0.412924 0.108 Uiso 1 1 calc R U . . .
H12C H 0.750143 0.059800 0.343080 0.108 Uiso 1 1 calc R U . . .
C13 C 0.3398(5) 0.2002(3) 0.2434(2) 0.0544(9) Uani 1 1 d . . . . .
C14 C 0.2508(5) 0.1976(3) 0.1717(2) 0.0542(8) Uani 1 1 d . . . . .
C15 C 0.2179(5) 0.1075(3) 0.1368(2) 0.0630(9) Uani 1 1 d . . . . .
H15 H 0.252117 0.047748 0.159138 0.076 Uiso 1 1 calc R U . . .
C16 C 0.1342(5) 0.1053(3) 0.0686(2) 0.0657(10) Uani 1 1 d . . . . .
H16 H 0.111406 0.044836 0.044697 0.079 Uiso 1 1 calc R U . . .
C17 C 0.0862(5) 0.1949(3) 0.0376(2) 0.0593(10) Uani 1 1 d . . . . .
C18 C 0.1177(5) 0.2847(3) 0.0708(2) 0.0637(10) Uani 1 1 d . . . . .
H18 H 0.083383 0.344175 0.048186 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2009(5) 0.2863(3) 0.1383(2) 0.0607(9) Uani 1 1 d . . . . .
H19 H 0.223673 0.347258 0.161487 0.073 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 111.4(3) . . ?
C8 N1 C9 125.2(3) . . ?
C1 N1 C9 122.8(3) . . ?
N3 N2 C13 101.6(3) . . ?
N4 N3 N2 114.3(3) . . ?
N4 N3 C11 122.6(3) . . ?
N2 N3 C11 123.1(3) . . ?
N3 N4 N5 105.8(3) . . ?
N4 N5 C13 106.4(3) . . ?
O3 N6 O4 122.8(4) . . ?
O3 N6 C17 118.6(4) . . ?
O4 N6 C17 118.6(4) . . ?
O1 C1 N1 124.4(4) . . ?
O1 C1 C2 129.3(4) . . ?
N1 C1 C2 106.3(3) . . ?
C3 C2 C7 121.8(4) . . ?
C3 C2 C1 130.3(4) . . ?
C7 C2 C1 107.9(3) . . ?
C2 C3 C4 117.7(4) . . ?
C3 C4 C5 120.8(4) . . ?
C4 C5 C6 122.0(4) . . ?
C7 C6 C5 116.4(4) . . ?
C2 C7 C6 121.4(4) . . ?
C2 C7 C8 108.4(3) . . ?
C6 C7 C8 130.2(4) . . ?
O2 C8 N1 125.3(4) . . ?
O2 C8 C7 128.9(4) . . ?
N1 C8 C7 105.8(3) . . ?
N1 C9 C10 112.6(3) . . ?
C11 C10 C9 115.1(3) . . ?
N3 C11 C10 109.4(3) . . ?
N3 C11 C12 110.0(3) . . ?
C10 C11 C12 112.5(3) . . ?
N2 C13 N5 111.9(4) . . ?
N2 C13 C14 124.3(3) . . ?
N5 C13 C14 123.8(3) . . ?
C15 C14 C19 119.7(4) . . ?
C15 C14 C13 120.6(3) . . ?
C19 C14 C13 119.7(3) . . ?
C14 C15 C16 120.5(3) . . ?
C17 C16 C15 117.9(4) . . ?
C18 C17 C16 122.6(4) . . ?
C18 C17 N6 118.9(4) . . ?
C16 C17 N6 118.4(4) . . ?
C17 C18 C19 119.1(4) . . ?
C18 C19 C14 120.1(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.203(4) . ?
O2 C8 1.204(4) . ?
O3 N6 1.218(4) . ?
O4 N6 1.230(4) . ?
N1 C8 1.380(4) . ?
N1 C1 1.393(5) . ?
N1 C9 1.465(4) . ?
N2 N3 1.319(4) . ?
N2 C13 1.333(4) . ?
N3 N4 1.316(4) . ?
N3 C11 1.473(4) . ?
N4 N5 1.317(5) . ?
N5 C13 1.344(5) . ?
N6 C17 1.469(5) . ?
C1 C2 1.470(5) . ?
C2 C3 1.370(5) . ?
C2 C7 1.372(5) . ?
C3 C4 1.370(6) . ?
C4 C5 1.372(6) . ?
C5 C6 1.390(6) . ?
C6 C7 1.373(5) . ?
C7 C8 1.482(5) . ?
C9 C10 1.518(5) . ?
C10 C11 1.508(5) . ?
C11 C12 1.518(5) . ?
C13 C14 1.462(5) . ?
C14 C15 1.379(5) . ?
C14 C19 1.381(5) . ?
C15 C16 1.387(5) . ?
C16 C17 1.369(5) . ?
C17 C18 1.360(5) . ?
C18 C19 1.373(5) . ?
