#------------------------------------------------------------------------------
#$Date: 2023-10-06 03:47:14 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286797 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159531.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_7159531
loop_
_publ_author_name
'Wang, Jiao-Mei'
'Zhao, Yu'
'Li, Wen-Ping'
'Kong, Xiang-Jun'
'Yao, Chang-Sheng'
'Zhang, Kai'
_publ_section_title
;
 Synthesis of tetracyclic dibenzo[b,f][1,4]oxazepine-fused
 β-lactams via visible-light-induced Staudinger annulation.
;
_journal_issue                   35
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7106
_journal_page_last               7114
_journal_paper_doi               10.1039/d3ob01078c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C22 H17 N O2'
_chemical_formula_weight         327.36
_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-2018/3
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.198(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.941(3)
_cell_length_b                   15.496(4)
_cell_length_c                   10.942(3)
_cell_measurement_reflns_used    10361
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      57.276
_cell_measurement_theta_min      4.585
_cell_volume                     1678.6(8)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10118
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.844
_diffrn_reflns_theta_min         2.629
_exptl_absorpt_coefficient_mu    0.083
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0500
_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)+(0.0622P)²+0.4105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1404
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2966
_reflns_number_total             4000
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01078c2.cif
_cod_data_source_block           ycs20230524shi2_0m
_cod_depositor_comments          'Adding full bibliography for 7159531.cif.'
_cod_original_cell_volume        1678.6(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159531
_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.
;
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 0.59418(14) 0.31302(10) 0.59059(14) 0.0766(4) Uani 1 1 d . . . . .
O2 O 0.91488(12) 0.35075(9) 0.28963(12) 0.0651(4) Uani 1 1 d . . . . .
N1 N 0.75779(13) 0.39447(9) 0.42474(12) 0.0469(3) Uani 1 1 d . . . . .
C1 C 0.7643(2) 0.33387(13) 0.75004(18) 0.0689(5) Uani 1 1 d . . . . .
H1 H 0.705901 0.311599 0.803841 0.083 Uiso 1 1 calc R U . . .
C2 C 0.8946(2) 0.35430(14) 0.79191(18) 0.0727(6) Uani 1 1 d . . . . .
H2 H 0.924292 0.345310 0.873974 0.087 Uiso 1 1 calc R U . . .
C3 C 0.9814(2) 0.38787(13) 0.71374(19) 0.0690(5) Uani 1 1 d . . . . .
H3 H 1.069838 0.401153 0.742482 0.083 Uiso 1 1 calc R U . . .
C4 C 0.93669(18) 0.40189(11) 0.59198(17) 0.0565(4) Uani 1 1 d . . . . .
H4 H 0.995188 0.425299 0.539141 0.068 Uiso 1 1 calc R U . . .
C5 C 0.80555(16) 0.38135(10) 0.54808(14) 0.0452(3) Uani 1 1 d . . . . .
C6 C 0.71940(17) 0.34641(10) 0.62727(15) 0.0508(4) Uani 1 1 d . . . . .
C7 C 0.49120(17) 0.34634(10) 0.51054(15) 0.0486(4) Uani 1 1 d . . . . .
C8 C 0.36529(18) 0.31579(11) 0.53662(17) 0.0563(4) Uani 1 1 d . . . . .
H8 H 0.358881 0.278787 0.602751 0.068 Uiso 1 1 calc R U . . .
C9 C 0.25081(18) 0.33972(12) 0.46580(18) 0.0614(5) Uani 1 1 d . . . . .
H9 H 0.167333 0.318093 0.483047 0.074 Uiso 1 1 calc R U . . .
C10 C 0.63341(15) 0.43684(9) 0.37348(13) 0.0415(3) Uani 1 1 d . . . . .
H10 H 0.638345 0.499152 0.388565 0.050 Uiso 1 1 calc R U . . .
C11 C 0.25898(18) 0.39585(13) 0.36886(19) 0.0632(5) Uani 1 1 d . . . . .
H11 H 0.181264 0.413263 0.321575 0.076 Uiso 1 1 calc R U . . .
C12 C 0.38400(17) 0.42581(11) 0.34304(16) 0.0545(4) Uani 1 1 d . . . . .
H12 H 0.389024 0.463861 0.277873 0.065 Uiso 1 1 calc R U . . .
C13 C 0.50322(15) 0.40105(9) 0.41123(14) 0.0438(3) Uani 1 1 d . . . . .
C14 C 0.67965(15) 0.41503(9) 0.24258(13) 0.0421(3) Uani 1 1 d . . . . .
C15 C 0.60238(19) 0.34134(11) 0.17541(17) 0.0581(4) Uani 1 1 d . . . . .
H15A H 0.592822 0.294472 0.231348 0.087 Uiso 1 1 calc R U . . .
H15B H 0.651141 0.321931 0.108751 0.087 Uiso 1 1 calc R U . . .
H15C H 0.514583 0.361295 0.143912 0.087 Uiso 1 1 calc R U . . .
C16 C 0.80899(16) 0.38078(10) 0.31493(14) 0.0460(4) Uani 1 1 d . . . . .
C17 C 0.70151(16) 0.49022(10) 0.15856(13) 0.0463(4) Uani 1 1 d . . . . .
C18 C 0.6367(2) 0.56878(11) 0.16595(16) 0.0571(4) Uani 1 1 d . . . . .
H18 H 0.575344 0.576792 0.224252 0.069 Uiso 1 1 calc R U . . .
C19 C 0.6624(3) 0.63585(13) 0.08704(19) 0.0745(6) Uani 1 1 d . . . . .
H19 H 0.619460 0.688752 0.093486 0.089 Uiso 1 1 calc R U . . .
C20 C 0.7512(3) 0.62394(16) -0.0004(2) 0.0833(7) Uani 1 1 d . . . . .
H20 H 0.768206 0.668778 -0.053350 0.100 Uiso 1 1 calc R U . . .
C21 C 0.8149(2) 0.54630(17) -0.00980(19) 0.0792(6) Uani 1 1 d . . . . .
H21 H 0.874507 0.538357 -0.069602 0.095 Uiso 1 1 calc R U . . .
C22 C 0.7910(2) 0.47979(13) 0.06899(16) 0.0634(5) Uani 1 1 d . . . . .
H22 H 0.835174 0.427339 0.062212 0.076 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'
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'
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
C6 O1 C7 129.97(13) . . ?
C16 N1 C5 134.73(14) . . ?
C16 N1 C10 95.84(12) . . ?
C5 N1 C10 129.24(12) . . ?
C2 C1 C6 120.11(18) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 120.51(18) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 119.69(19) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.53(17) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 119.32(15) . . ?
C6 C5 N1 118.96(15) . . ?
C4 C5 N1 121.71(14) . . ?
O1 C6 C5 124.10(15) . . ?
O1 C6 C1 115.65(16) . . ?
C5 C6 C1 119.82(17) . . ?
O1 C7 C8 111.74(15) . . ?
O1 C7 C13 127.58(14) . . ?
C8 C7 C13 120.64(16) . . ?
C9 C8 C7 120.59(17) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C11 120.14(16) . . ?
C8 C9 H9 119.9 . . ?
C11 C9 H9 119.9 . . ?
N1 C10 C13 116.61(12) . . ?
N1 C10 C14 86.93(10) . . ?
C13 C10 C14 119.98(12) . . ?
N1 C10 H10 110.4 . . ?
C13 C10 H10 110.4 . . ?
C14 C10 H10 110.4 . . ?
C12 C11 C9 119.10(18) . . ?
C12 C11 H11 120.4 . . ?
C9 C11 H11 120.4 . . ?
C11 C12 C13 122.34(17) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C7 C13 C12 117.13(15) . . ?
C7 C13 C10 125.27(14) . . ?
C12 C13 C10 117.58(14) . . ?
C17 C14 C15 112.16(13) . . ?
C17 C14 C16 114.73(13) . . ?
C15 C14 C16 110.46(13) . . ?
C17 C14 C10 117.13(12) . . ?
C15 C14 C10 114.92(12) . . ?
C16 C14 C10 84.60(11) . . ?
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 . . ?
O2 C16 N1 131.74(16) . . ?
O2 C16 C14 136.03(15) . . ?
N1 C16 C14 92.20(11) . . ?
C18 C17 C22 118.31(16) . . ?
C18 C17 C14 123.32(14) . . ?
C22 C17 C14 118.37(15) . . ?
C17 C18 C19 120.60(18) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.16(19) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C21 C22 C17 120.7(2) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?
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 C6 1.374(2) . ?
O1 C7 1.385(2) . ?
O2 C16 1.2059(18) . ?
N1 C16 1.3633(19) . ?
N1 C5 1.404(2) . ?
N1 C10 1.4659(19) . ?
C1 C2 1.371(3) . ?
C1 C6 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C7 C8 1.392(2) . ?
C7 C13 1.392(2) . ?
C8 C9 1.369(3) . ?
C8 H8 0.9300 . ?
C9 C11 1.380(3) . ?
C9 H9 0.9300 . ?
C10 C13 1.500(2) . ?
C10 C14 1.5800(19) . ?
C10 H10 0.9800 . ?
C11 C12 1.380(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.396(2) . ?
C12 H12 0.9300 . ?
C14 C17 1.512(2) . ?
C14 C15 1.527(2) . ?
C14 C16 1.542(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 C18 1.383(2) . ?
C17 C22 1.391(2) . ?
C18 C19 1.390(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
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
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 N1 -179.65(16) . . . . ?
C16 N1 C5 C6 -136.72(18) . . . . ?
C10 N1 C5 C6 49.5(2) . . . . ?
C16 N1 C5 C4 42.8(3) . . . . ?
C10 N1 C5 C4 -130.98(17) . . . . ?
C7 O1 C6 C5 -46.4(3) . . . . ?
C7 O1 C6 C1 141.29(18) . . . . ?
C4 C5 C6 O1 -170.83(16) . . . . ?
N1 C5 C6 O1 8.7(2) . . . . ?
C4 C5 C6 C1 1.2(2) . . . . ?
N1 C5 C6 C1 -179.24(15) . . . . ?
C2 C1 C6 O1 171.26(18) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C6 O1 C7 C8 -153.69(18) . . . . ?
C6 O1 C7 C13 28.7(3) . . . . ?
O1 C7 C8 C9 -178.45(16) . . . . ?
C13 C7 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 C11 -1.2(3) . . . . ?
C16 N1 C10 C13 127.37(13) . . . . ?
C5 N1 C10 C13 -57.1(2) . . . . ?
C16 N1 C10 C14 5.18(12) . . . . ?
C5 N1 C10 C14 -179.26(15) . . . . ?
C8 C9 C11 C12 1.4(3) . . . . ?
C9 C11 C12 C13 0.3(3) . . . . ?
O1 C7 C13 C12 179.65(16) . . . . ?
C8 C7 C13 C12 2.3(2) . . . . ?
O1 C7 C13 C10 -1.7(3) . . . . ?
C8 C7 C13 C10 -179.10(14) . . . . ?
C11 C12 C13 C7 -2.1(2) . . . . ?
C11 C12 C13 C10 179.15(15) . . . . ?
N1 C10 C13 C7 16.2(2) . . . . ?
C14 C10 C13 C7 118.87(17) . . . . ?
N1 C10 C13 C12 -165.19(13) . . . . ?
C14 C10 C13 C12 -62.50(19) . . . . ?
N1 C10 C14 C17 -119.64(14) . . . . ?
C13 C10 C14 C17 121.22(15) . . . . ?
N1 C10 C14 C15 105.49(14) . . . . ?
C13 C10 C14 C15 -13.6(2) . . . . ?
N1 C10 C14 C16 -4.58(10) . . . . ?
C13 C10 C14 C16 -123.71(14) . . . . ?
C5 N1 C16 O2 1.3(3) . . . . ?
C10 N1 C16 O2 176.43(18) . . . . ?
C5 N1 C16 C14 179.53(17) . . . . ?
C10 N1 C16 C14 -5.30(12) . . . . ?
C17 C14 C16 O2 -59.5(2) . . . . ?
C15 C14 C16 O2 68.4(2) . . . . ?
C10 C14 C16 O2 -177.0(2) . . . . ?
C17 C14 C16 N1 122.35(13) . . . . ?
C15 C14 C16 N1 -109.69(13) . . . . ?
C10 C14 C16 N1 4.92(11) . . . . ?
C15 C14 C17 C18 109.82(18) . . . . ?
C16 C14 C17 C18 -123.09(17) . . . . ?
C10 C14 C17 C18 -26.2(2) . . . . ?
C15 C14 C17 C22 -69.96(19) . . . . ?
C16 C14 C17 C22 57.13(19) . . . . ?
C10 C14 C17 C22 154.00(15) . . . . ?
C22 C17 C18 C19 -1.1(3) . . . . ?
C14 C17 C18 C19 179.15(16) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C17 0.4(3) . . . . ?
C18 C17 C22 C21 0.4(3) . . . . ?
C14 C17 C22 C21 -179.84(18) . . . . ?
