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#$Date: 2024-03-04 22:02:57 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290127 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/07/1570784.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_1570784
loop_
_publ_author_name
'He, Yi'
'Wang, Juanjuan'
'Zhu, Tongtong'
'Zheng, Zhaojing'
'Wei, Hao'
_publ_section_title
;
 Nitrogen atom insertion into arenols to access benzazepines.
;
_journal_issue                   7
_journal_name_full               'Chemical science'
_journal_page_first              2612
_journal_page_last               2617
_journal_paper_doi               10.1039/d3sc05367a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C15 H12 N2 O3'
_chemical_formula_sum            'C15 H12 N2 O3'
_chemical_formula_weight         268.27
_chemical_name_systematic        375
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2023-05-15 deposited with the CCDC.	2024-01-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.727(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7369(6)
_cell_length_b                   9.7927(9)
_cell_length_c                   16.8291(16)
_cell_measurement_reflns_used    16902
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      53.90
_cell_measurement_theta_min      2.32
_cell_volume                     1252.78(19)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.1040
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16086
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.898
_diffrn_reflns_theta_min         5.955
_exptl_absorpt_coefficient_mu    0.535
_exptl_absorpt_correction_T_max  0.7506
_exptl_absorpt_correction_T_min  0.5060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       Block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.125
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2215
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1478
_refine_ls_R_factor_gt           0.0935
_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)+(0.1560P)²+2.7449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2433
_refine_ls_wR_factor_ref         0.3017
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1513
_reflns_number_total             2215
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05367a2.cif
_cod_data_source_block           1_CCDC2
_cod_depositor_comments
'Adding full bibliography for 1570782--1570784.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1570784
_shelx_shelxl_version_number     2016/6
_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   0.934
_shelx_estimated_absorpt_t_max   0.948
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.9138(4) 0.7542(4) 0.3848(2) 0.0504(11) Uani 1 1 d . . . . .
O2 O 0.8196(4) 0.5003(4) 0.2958(2) 0.0459(10) Uani 1 1 d . . . . .
O3 O 0.8923(4) 0.3411(3) 0.39259(19) 0.0387(10) Uani 1 1 d . . . . .
N2 N 0.7568(4) 0.4918(4) 0.4937(2) 0.0325(10) Uani 1 1 d . . . . .
C5 C 0.6968(3) 0.5520(3) 0.55985(13) 0.0324(11) Uani 1 1 d G . . . .
C4 C 0.6002(3) 0.6718(3) 0.55943(13) 0.0323(11) Uani 1 1 d G . . . .
C3 C 0.5456(3) 0.7149(3) 0.62948(16) 0.0377(12) Uani 1 1 d G . . . .
H3 H 0.481025 0.795096 0.629194 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5876(4) 0.6383(3) 0.69995(13) 0.0414(13) Uani 1 1 d G . . . .
H2 H 0.551023 0.667158 0.746819 0.050 Uiso 1 1 calc R U . . .
C1 C 0.6841(4) 0.5185(3) 0.70038(13) 0.0426(13) Uani 1 1 d G . . . .
H1 H 0.712163 0.467222 0.747527 0.051 Uiso 1 1 calc R U . . .
C6 C 0.7387(4) 0.4754(3) 0.63033(16) 0.0380(12) Uani 1 1 d G . . . .
H6 H 0.803306 0.395222 0.630610 0.046 Uiso 1 1 calc R U . . .
C9 C 0.5530(4) 0.8817(4) 0.3799(2) 0.0420(13) Uani 1 1 d G . . . .
H9 H 0.590360 0.923221 0.336339 0.050 Uiso 1 1 calc R U . . .
N1 N 0.5436(3) 0.7475(3) 0.48709(17) 0.0330(10) Uani 1 1 d G . . . .
C7 C 0.3908(4) 0.8250(4) 0.47241(19) 0.0409(13) Uani 1 1 d G . . . .
H7 H 0.300360 0.821847 0.501827 0.049 Uiso 1 1 calc R U . . .
C8 C 0.3967(4) 0.9079(4) 0.4062(2) 0.0435(13) Uani 1 1 d G . . . .
H8 H 0.310936 0.970198 0.383413 0.052 Uiso 1 1 calc R U . . .
C10 C 0.6439(4) 0.7825(3) 0.42990(18) 0.0346(12) Uani 1 1 d G . . . .
C11 C 0.7966(6) 0.7046(5) 0.4155(3) 0.0378(12) Uani 1 1 d . . . . .
C12 C 0.7940(5) 0.5533(5) 0.4324(3) 0.0329(11) Uani 1 1 d . . . . .
C13 C 0.8391(5) 0.4647(5) 0.3653(3) 0.0359(12) Uani 1 1 d . . . . .
C14 C 0.9218(7) 0.2409(6) 0.3326(3) 0.0452(13) Uani 1 1 d . . . . .
H14A H 1.019245 0.268745 0.307438 0.054 Uiso 1 1 calc R U . . .
H14B H 0.817557 0.231858 0.290819 0.054 Uiso 1 1 calc R U . . .
C15 C 0.9626(7) 0.1086(6) 0.3760(3) 0.0517(15) Uani 1 1 d . . . . .
H15A H 0.981634 0.039280 0.338254 0.078 Uiso 1 1 calc R U . . .
H15B H 0.865666 0.082688 0.401100 0.078 Uiso 1 1 calc R U . . .
H15C H 1.066600 0.118626 0.416747 0.078 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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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
C13 O3 C14 116.8(4) . . ?
C12 N2 C5 126.7(4) . . ?
C4 C5 C6 120.0 . . ?
C4 C5 N2 127.1(2) . . ?
C6 C5 N2 112.8(2) . . ?
C5 C4 C3 120.0 . . ?
C5 C4 N1 121.6(2) . . ?
C3 C4 N1 118.3(2) . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C1 C6 120.0 . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C6 C5 120.0 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C9 C10 108.0 . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
C10 N1 C7 108.0 . . ?
C10 N1 C4 126.8(2) . . ?
C7 N1 C4 123.6(2) . . ?
C8 C7 N1 108.0 . . ?
C8 C7 H7 126.0 . . ?
N1 C7 H7 126.0 . . ?
C7 C8 C9 108.0 . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
N1 C10 C9 108.0 . . ?
N1 C10 C11 123.9(3) . . ?
C9 C10 C11 126.7(3) . . ?
O1 C11 C10 123.1(5) . . ?
O1 C11 C12 120.4(4) . . ?
C10 C11 C12 116.2(4) . . ?
N2 C12 C11 129.1(4) . . ?
N2 C12 C13 116.8(4) . . ?
C11 C12 C13 114.1(4) . . ?
O2 C13 O3 125.0(5) . . ?
O2 C13 C12 123.7(5) . . ?
O3 C13 C12 111.3(4) . . ?
O3 C14 C15 106.9(4) . . ?
O3 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O3 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 C11 1.225(6) . ?
O2 C13 1.203(5) . ?
O3 C13 1.333(6) . ?
O3 C14 1.456(6) . ?
N2 C12 1.273(6) . ?
N2 C5 1.413(4) . ?
C5 C4 1.3900 . ?
C5 C6 1.3900 . ?
C4 C3 1.3900 . ?
C4 N1 1.423(3) . ?
C3 C2 1.3900 . ?
C3 H3 0.9300 . ?
C2 C1 1.3900 . ?
C2 H2 0.9300 . ?
C1 C6 1.3900 . ?
C1 H1 0.9300 . ?
C6 H6 0.9300 . ?
C9 C8 1.387(2) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9300 . ?
N1 C10 1.387(2) . ?
N1 C7 1.388(2) . ?
C7 C8 1.386(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.464(6) . ?
C11 C12 1.509(7) . ?
C12 C13 1.516(7) . ?
C14 C15 1.492(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
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
C12 N2 C5 C4 28.4(5) . . . . ?
C12 N2 C5 C6 -153.8(3) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
N2 C5 C4 C3 177.7(3) . . . . ?
C6 C5 C4 N1 -175.2(3) . . . . ?
N2 C5 C4 N1 2.4(3) . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
N1 C4 C3 C2 175.4(3) . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C3 C2 C1 C6 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
N2 C5 C6 C1 -178.0(3) . . . . ?
C5 C4 N1 C10 -46.3(4) . . . . ?
C3 C4 N1 C10 138.4(2) . . . . ?
C5 C4 N1 C7 149.6(2) . . . . ?
C3 C4 N1 C7 -25.8(3) . . . . ?
C10 N1 C7 C8 0.0 . . . . ?
C4 N1 C7 C8 166.7(3) . . . . ?
N1 C7 C8 C9 0.0 . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C7 N1 C10 C9 0.0 . . . . ?
C4 N1 C10 C9 -166.2(3) . . . . ?
C7 N1 C10 C11 -167.4(4) . . . . ?
C4 N1 C10 C11 26.4(4) . . . . ?
C8 C9 C10 N1 0.0 . . . . ?
C8 C9 C10 C11 167.0(4) . . . . ?
N1 C10 C11 O1 -157.0(4) . . . . ?
C9 C10 C11 O1 38.0(6) . . . . ?
N1 C10 C11 C12 29.4(5) . . . . ?
C9 C10 C11 C12 -135.6(3) . . . . ?
C5 N2 C12 C11 4.4(6) . . . . ?
C5 N2 C12 C13 -174.2(3) . . . . ?
O1 C11 C12 N2 139.3(5) . . . . ?
C10 C11 C12 N2 -46.9(6) . . . . ?
O1 C11 C12 C13 -42.0(6) . . . . ?
C10 C11 C12 C13 131.8(4) . . . . ?
C14 O3 C13 O2 -2.6(6) . . . . ?
C14 O3 C13 C12 173.6(4) . . . . ?
N2 C12 C13 O2 154.2(4) . . . . ?
C11 C12 C13 O2 -24.6(6) . . . . ?
N2 C12 C13 O3 -22.1(5) . . . . ?
C11 C12 C13 O3 159.1(3) . . . . ?
C13 O3 C14 C15 -174.5(4) . . . . ?
