#------------------------------------------------------------------------------
#$Date: 2024-08-05 22:56:11 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293919 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160019.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_7160019
loop_
_publ_author_name
'Ren, Shaobo'
'Zhu, Jian'
'Liu, Yunkui'
_publ_section_title
;
 Trifunctionalization of CC bonds in vinyl azides to access
 densely functionalized phenanthridines enabled by the
 NCS/AgNO₂ system.
;
_journal_issue                   29
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5982
_journal_page_last               5986
_journal_paper_doi               10.1039/d4ob00905c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C15 H10 Cl2 N2 O2'
_chemical_formula_sum            'C15 H10 Cl2 N2 O2'
_chemical_formula_weight         321.15
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-04-16 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0880(7)
_cell_length_b                   6.8830(4)
_cell_length_c                   18.0810(9)
_cell_measurement_reflns_used    7235
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.2
_cell_volume                     1379.92(14)
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12881
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_T_max  0.9110
_exptl_absorpt_correction_T_min  0.7861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Higashi, T.(1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0661P)²+1.2724P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1590
_reflns_number_gt                1081
_reflns_number_total             1701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob00905c2.cif
_cod_data_source_block           rsb-1
_cod_depositor_comments          'Adding full bibliography for 7160019.cif.'
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               7160019
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2878(3) 0.2500 0.39063(19) 0.0437(8) Uani 1 2 d S . .
C2 C 0.2353(3) 0.2500 0.46289(19) 0.0440(8) Uani 1 2 d S . .
C3 C 0.1094(4) 0.2500 0.4746(2) 0.0672(12) Uani 1 2 d S . .
H3 H 0.0579 0.2500 0.4340 0.081 Uiso 1 2 calc SR . .
C4 C 0.0618(5) 0.2500 0.5440(3) 0.0738(14) Uani 1 2 d S . .
H4 H -0.0213 0.2500 0.5506 0.089 Uiso 1 2 calc SR . .
C5 C 0.1372(5) 0.2500 0.6041(3) 0.0700(13) Uani 1 2 d S . .
H5 H 0.1047 0.2500 0.6515 0.084 Uiso 1 2 calc SR . .
C6 C 0.2597(4) 0.2500 0.5950(2) 0.0603(11) Uani 1 2 d S . .
H6 H 0.3086 0.2500 0.6368 0.072 Uiso 1 2 calc SR . .
C7 C 0.3144(3) 0.2500 0.52489(18) 0.0428(8) Uani 1 2 d S . .
C8 C 0.4452(3) 0.2500 0.51185(19) 0.0409(8) Uani 1 2 d S . .
C9 C 0.5379(4) 0.2500 0.56674(19) 0.0479(9) Uani 1 2 d S . .
C10 C 0.6567(4) 0.2500 0.5432(2) 0.0539(10) Uani 1 2 d S . .
H10 H 0.7169 0.2500 0.5790 0.065 Uiso 1 2 calc SR . .
C11 C 0.6913(4) 0.2500 0.4696(2) 0.0551(10) Uani 1 2 d S . .
H11 H 0.7725 0.2500 0.4566 0.066 Uiso 1 2 calc SR . .
C12 C 0.6038(3) 0.2500 0.4165(2) 0.0489(9) Uani 1 2 d S . .
H12 H 0.6251 0.2500 0.3667 0.059 Uiso 1 2 calc SR . .
C13 C 0.4823(3) 0.2500 0.43695(17) 0.0397(8) Uani 1 2 d S . .
C14 C 0.5188(5) 0.2500 0.6490(2) 0.0687(13) Uani 1 2 d S . .
H14A H 0.4694 0.1431 0.6647 0.103 Uiso 1 1 d R . .
H14B H 0.5992 0.2500 0.6688 0.103 Uiso 1 2 d SR . .
C15 C 0.2132(4) 0.2500 0.3199(2) 0.0530(10) Uani 1 2 d S . .
N2 N 0.3004(4) 0.2500 0.2519(2) 0.0727(11) Uani 1 2 d S . .
N1 N 0.4024(3) 0.2500 0.37763(15) 0.0433(7) Uani 1 2 d S . .
O1 O 0.3307(3) 0.0934(6) 0.22977(16) 0.1199(13) Uani 1 1 d . . .
Cl1 Cl 0.12356(10) 0.04104(18) 0.31153(5) 0.0957(5) Uani 1 1 d . . .
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'
H H 0.0000 0.0000 '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'
Cl Cl 0.1484 0.1585 '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
N1 C1 C2 124.5(3) . . ?
N1 C1 C15 112.4(3) . . ?
C2 C1 C15 123.1(3) . . ?
C3 C2 C7 119.4(3) . . ?
C3 C2 C1 122.6(3) . . ?
C7 C2 C1 118.0(3) . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.6(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 122.5(4) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C2 116.4(4) . . ?
C6 C7 C8 124.8(3) . . ?
C2 C7 C8 118.8(3) . . ?
C13 C8 C9 117.1(3) . . ?
C13 C8 C7 116.1(3) . . ?
C9 C8 C7 126.8(3) . . ?
C10 C9 C8 118.1(3) . . ?
C10 C9 C14 116.0(4) . . ?
C8 C9 C14 125.9(4) . . ?
C9 C10 C11 124.0(4) . . ?
C9 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
C12 C11 C10 118.6(4) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C13 120.0(4) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N1 C13 C12 114.2(3) . . ?
N1 C13 C8 123.6(3) . . ?
C12 C13 C8 122.2(3) . . ?
C9 C14 H14A 111.9 . . ?
C9 C14 H14B 103.7 . . ?
H14A C14 H14B 114.8 . . ?
C1 C15 N2 108.9(3) . . ?
C1 C15 Cl1 112.31(15) . . ?
N2 C15 Cl1 106.41(16) . . ?
C1 C15 Cl1 112.31(15) . 8_565 ?
N2 C15 Cl1 106.41(16) . 8_565 ?
Cl1 C15 Cl1 110.1(2) . 8_565 ?
O1 N2 O1 128.3(5) 8_565 . ?
O1 N2 C15 115.8(3) 8_565 . ?
O1 N2 C15 115.8(3) . . ?
C1 N1 C13 119.1(3) . . ?
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
C1 N1 1.293(5) . ?
C1 C2 1.430(5) . ?
C1 C15 1.523(5) . ?
C2 C3 1.412(6) . ?
C2 C7 1.423(5) . ?
C3 C4 1.360(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.469(5) . ?
C8 C13 1.415(5) . ?
C8 C9 1.429(5) . ?
C9 C10 1.384(6) . ?
C9 C14 1.503(5) . ?
C10 C11 1.386(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(5) . ?
C12 H12 0.9300 . ?
C13 N1 1.391(4) . ?
C14 H14A 0.9602 . ?
C14 H14B 0.9602 . ?
C15 N2 1.565(6) . ?
C15 Cl1 1.755(2) . ?
C15 Cl1 1.755(2) 8_565 ?
N2 O1 1.198(4) 8_565 ?
N2 O1 1.198(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 180.0 . . . . ?
C15 C1 C2 C3 0.0 . . . . ?
N1 C1 C2 C7 0.0 . . . . ?
C15 C1 C2 C7 180.0 . . . . ?
C7 C2 C3 C4 0.000(1) . . . . ?
C1 C2 C3 C4 180.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C4 C5 C6 C7 0.000(2) . . . . ?
C5 C6 C7 C2 0.000(1) . . . . ?
C5 C6 C7 C8 180.000(1) . . . . ?
C3 C2 C7 C6 0.000(1) . . . . ?
C1 C2 C7 C6 180.0 . . . . ?
C3 C2 C7 C8 180.0 . . . . ?
C1 C2 C7 C8 0.0 . . . . ?
C6 C7 C8 C13 180.0 . . . . ?
C2 C7 C8 C13 0.0 . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C2 C7 C8 C9 180.0 . . . . ?
C13 C8 C9 C10 0.000(1) . . . . ?
C7 C8 C9 C10 180.0 . . . . ?
C13 C8 C9 C14 180.000(1) . . . . ?
C7 C8 C9 C14 0.000(1) . . . . ?
C8 C9 C10 C11 0.000(1) . . . . ?
C14 C9 C10 C11 180.0 . . . . ?
C9 C10 C11 C12 0.000(1) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 N1 180.0 . . . . ?
C11 C12 C13 C8 0.0 . . . . ?
C9 C8 C13 N1 180.0 . . . . ?
C7 C8 C13 N1 0.0 . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
C7 C8 C13 C12 180.0 . . . . ?
N1 C1 C15 N2 0.0 . . . . ?
C2 C1 C15 N2 180.0 . . . . ?
N1 C1 C15 Cl1 117.61(19) . . . . ?
C2 C1 C15 Cl1 -62.39(19) . . . . ?
N1 C1 C15 Cl1 -117.61(19) . . . 8_565 ?
C2 C1 C15 Cl1 62.39(19) . . . 8_565 ?
C1 C15 N2 O1 -89.1(3) . . . 8_565 ?
Cl1 C15 N2 O1 149.6(3) . . . 8_565 ?
Cl1 C15 N2 O1 32.2(4) 8_565 . . 8_565 ?
C1 C15 N2 O1 89.1(3) . . . . ?
Cl1 C15 N2 O1 -32.2(4) . . . . ?
Cl1 C15 N2 O1 -149.6(3) 8_565 . . . ?
C2 C1 N1 C13 0.0 . . . . ?
C15 C1 N1 C13 180.0 . . . . ?
C12 C13 N1 C1 180.0 . . . . ?
C8 C13 N1 C1 0.0 . . . . ?
