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#$Date: 2022-08-06 15:02:35 +0300 (Sat, 06 Aug 2022) $
#$Revision: 277136 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158761.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_7158761
loop_
_publ_author_name
'Singh, Shashank'
'Tripathi, Krishna N.'
'Singh, Ravi P.'
_publ_section_title
;
 Redox activated amines in the organophotoinduced alkylation of coumarins.
;
_journal_issue                   29
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5716
_journal_page_last               5720
_journal_paper_doi               10.1039/d2ob00943a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C15 H13 N O2'
_chemical_formula_sum            'C15 H13 N O2'
_chemical_formula_weight         239.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-09-20 deposited with the CCDC.	2022-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.673(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.805(3)
_cell_length_b                   6.864(2)
_cell_length_c                   10.545(4)
_cell_measurement_reflns_used    4304
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      3.74
_cell_volume                     596.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15717
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.340
_diffrn_reflns_theta_min         2.472
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             252.0
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   0.986
_exptl_transmission_factor_min   0.981
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         1603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0607
_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)+(0.1000P)²+0.1791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.2048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1172
_reflns_number_total             1611
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00943a2.cif
_cod_data_source_block           KNT7220_0m_a
_cod_depositor_comments
'Adding full bibliography for 7158761--7158762.cif.'
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7158761
_shelx_shelxl_version_number     2014/7
_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, y+1/2, -z'
'-x, -y, -z'
'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_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
O2 O 0.4358(2) 0.2500 0.56821(17) 0.0528(5) Uani 1 2 d S T P . .
O1 O 0.1787(2) 0.2500 0.4366(2) 0.0665(6) Uani 1 2 d S T P . .
C10 C 0.5314(3) 0.2500 0.3402(2) 0.0390(5) Uani 1 2 d S T P . .
N1 N 0.1450(3) 0.2500 0.0934(3) 0.0691(8) Uani 1 2 d S T P . .
C5 C 0.6526(3) 0.2500 0.4762(2) 0.0415(5) Uani 1 2 d S T P . .
C8 C 0.3726(3) 0.2500 0.3277(2) 0.0403(5) Uani 1 2 d S T P . .
C11 C 0.5759(3) 0.2500 0.2148(2) 0.0486(6) Uani 1 2 d S T P . .
H11 H 0.4735 0.2500 0.1373 0.058 Uiso 1 2 calc R U P . .
C6 C 0.5987(3) 0.2500 0.5853(2) 0.0459(6) Uani 1 2 d S T P . .
C9 C 0.2437(3) 0.2500 0.1977(3) 0.0486(6) Uani 1 2 d S T P . .
C7 C 0.3170(3) 0.2500 0.4432(3) 0.0460(6) Uani 1 2 d S T P . .
C4 C 0.8214(3) 0.2500 0.5061(3) 0.0533(7) Uani 1 2 d S T P . .
H4 H 0.8617 0.2500 0.4356 0.064 Uiso 1 2 calc R U P . .
C12 C 0.6730(2) 0.4289(3) 0.1971(2) 0.0593(6) Uani 1 1 d . . . . .
H12A H 0.6006 0.5316 0.1476 0.071 Uiso 1 1 calc R U . . .
H12B H 0.7420 0.4792 0.2843 0.071 Uiso 1 1 calc R U . . .
C3 C 0.9277(4) 0.2500 0.6376(3) 0.0667(8) Uani 1 2 d S T P . .
H3 H 1.0390 0.2500 0.6556 0.080 Uiso 1 2 calc R U P . .
C1 C 0.7057(4) 0.2500 0.7184(3) 0.0620(8) Uani 1 2 d S T P . .
H1 H 0.6664 0.2500 0.7895 0.074 Uiso 1 2 calc R U P . .
C2 C 0.8691(4) 0.2500 0.7444(3) 0.0710(9) Uani 1 2 d S T P . .
H2 H 0.9414 0.2500 0.8334 0.085 Uiso 1 2 calc R U P . .
C13 C 0.7724(4) 0.3537(5) 0.1186(3) 0.1041(10) Uani 1 1 d . . . . .
H13A H 0.7282 0.4012 0.0261 0.125 Uiso 1 1 calc R U . . .
H13B H 0.8829 0.4012 0.1588 0.125 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
C7 O2 C6 122.22(18) . . ?
C8 C10 C5 117.9(2) . . ?
C8 C10 C11 119.5(2) . . ?
C5 C10 C11 122.6(2) . . ?
C6 C5 C4 117.1(2) . . ?
C6 C5 C10 118.1(2) . . ?
C4 C5 C10 124.8(2) . . ?
C10 C8 C9 122.1(2) . . ?
C10 C8 C7 123.7(2) . . ?
C9 C8 C7 114.2(2) . . ?
C10 C11 C12 115.66(14) . . ?
C10 C11 C12 115.66(14) . 4_565 ?
C12 C11 C12 105.3(2) . 4_565 ?
C10 C11 H11 106.5 . . ?
C12 C11 H11 106.5 . . ?
C12 C11 H11 106.5 4_565 . ?
O2 C6 C1 115.8(2) . . ?
O2 C6 C5 122.2(2) . . ?
C1 C6 C5 122.0(3) . . ?
N1 C9 C8 178.2(3) . . ?
O1 C7 O2 118.3(2) . . ?
O1 C7 C8 125.8(2) . . ?
O2 C7 C8 115.9(2) . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C13 C12 C11 104.51(19) . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.9 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C1 C6 119.6(3) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C13 C13 C12 110.22(14) 4_565 . ?
C13 C13 H13A 109.6 4_565 . ?
C12 C13 H13A 109.6 . . ?
C13 C13 H13B 109.6 4_565 . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
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
O2 C7 1.363(3) . ?
O2 C6 1.381(3) . ?
O1 C7 1.195(3) . ?
C10 C8 1.358(3) . ?
C10 C5 1.454(3) . ?
C10 C11 1.505(3) . ?
N1 C9 1.136(3) . ?
C5 C6 1.391(3) . ?
C5 C4 1.407(4) . ?
C8 C9 1.439(3) . ?
C8 C7 1.464(3) . ?
C11 C12 1.545(2) . ?
C11 C12 1.545(2) 4_565 ?
C11 H11 0.9800 . ?
C6 C1 1.386(3) . ?
C4 C3 1.372(4) . ?
C4 H4 0.9300 . ?
C12 C13 1.492(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C3 C2 1.394(5) . ?
C3 H3 0.9300 . ?
C1 C2 1.367(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C13 C13 1.424(6) 4_565 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
