#------------------------------------------------------------------------------
#$Date: 2019-12-19 02:22:05 +0200 (Thu, 19 Dec 2019) $
#$Revision: 245358 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/77/4037706.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_4037706
loop_
_publ_author_name
'Tripathi, Krishna N.'
'Belal, Md'
'Singh, Ravi P.'
_publ_section_title
;
 Organo Photoinduced Decarboxylative Alkylation of Coumarins with
 N-(Acyloxy)phthalimide.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b00977
_journal_year                    2019
_chemical_formula_moiety         'C12 H9 N O2'
_chemical_formula_sum            'C12 H9 N O2'
_chemical_formula_weight         199.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                74.721(15)
_cell_angle_beta                 66.617(15)
_cell_angle_gamma                61.920(14)
_cell_formula_units_Z            2
_cell_length_a                   8.020(5)
_cell_length_b                   8.024(5)
_cell_length_c                   9.517(5)
_cell_measurement_reflns_used    2342
_cell_measurement_temperature    161(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      2.34
_cell_volume                     493.7(5)
_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      161(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_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  0.0650
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8123
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.015
_diffrn_reflns_theta_min         2.890
_exptl_absorpt_coefficient_mu    0.092
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.697
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.697
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0520
_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+0.7499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1185
_reflns_number_total             2372
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00977_si_005.cif
_cod_data_source_block           KT09_0ma_a_a
_cod_database_code               4037706
_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, -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
O2 O 0.7503(3) 0.5373(3) 0.5816(2) 0.0537(5) Uani 1 1 d . .
O1 O 0.8284(3) 0.3122(3) 0.7647(3) 0.0754(8) Uani 1 1 d . .
C9 C 0.4093(3) 0.7119(3) 0.5810(3) 0.0378(5) Uani 1 1 d . .
C1 C 0.3457(3) 0.6063(3) 0.7238(3) 0.0383(5) Uani 1 1 d . .
C4 C 0.6113(4) 0.6750(4) 0.5150(3) 0.0418(6) Uani 1 1 d . .
C2 C 0.4869(4) 0.4738(4) 0.7866(3) 0.0423(6) Uani 1 1 d . .
C8 C 0.2810(4) 0.8526(4) 0.5024(3) 0.0481(6) Uani 1 1 d . .
H8 H 0.1424 0.8814 0.5429 0.058 Uiso 1 1 calc R U
C10 C 0.1291(4) 0.6481(4) 0.8033(3) 0.0468(6) Uani 1 1 d . .
H10A H 0.1161 0.5360 0.8731 0.056 Uiso 1 1 calc R U
H10B H 0.0645 0.6731 0.7258 0.056 Uiso 1 1 calc R U
C5 C 0.6847(4) 0.7721(4) 0.3796(3) 0.0502(7) Uani 1 1 d . .
H5 H 0.8230 0.7443 0.3378 0.060 Uiso 1 1 calc R U
N1 N 0.3986(5) 0.2805(4) 1.0457(3) 0.0799(9) Uani 1 1 d . .
C6 C 0.5535(4) 0.9093(4) 0.3068(3) 0.0544(7) Uani 1 1 d . .
H6 H 0.6015 0.9773 0.2137 0.065 Uiso 1 1 calc R U
C12 C 0.4385(4) 0.3642(4) 0.9303(3) 0.0532(7) Uani 1 1 d . .
C3 C 0.6981(4) 0.4319(4) 0.7153(3) 0.0508(7) Uani 1 1 d . .
C7 C 0.3526(5) 0.9495(4) 0.3677(3) 0.0551(7) Uani 1 1 d . .
H7 H 0.2633 1.0446 0.3162 0.066 Uiso 1 1 calc R U
C11 C 0.0231(5) 0.8197(5) 0.8957(4) 0.0659(9) Uani 1 1 d . .
H11A H 0.0806 0.7918 0.9772 0.099 Uiso 1 1 calc R U
H11B H -0.1193 0.8476 0.9417 0.099 Uiso 1 1 calc R U
H11C H 0.0400 0.9298 0.8275 0.099 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
C3 O2 C4 122.0(2)
C4 C9 C8 116.7(2)
C4 C9 C1 118.8(2)
C8 C9 C1 124.5(2)
C2 C1 C9 117.9(2)
C2 C1 C10 121.3(2)
C9 C1 C10 120.7(2)
O2 C4 C5 116.0(2)
O2 C4 C9 121.4(2)
C5 C4 C9 122.6(2)
C1 C2 C12 122.3(2)
C1 C2 C3 123.1(2)
C12 C2 C3 114.6(2)
C7 C8 C9 121.1(3)
C7 C8 H8 119.5
C9 C8 H8 119.5
C1 C10 C11 111.4(2)
C1 C10 H10A 109.4
C11 C10 H10A 109.4
C1 C10 H10B 109.4
C11 C10 H10B 109.4
H10A C10 H10B 108.0
C6 C5 C4 118.6(3)
C6 C5 H5 120.7
C4 C5 H5 120.7
C5 C6 C7 120.6(3)
C5 C6 H6 119.7
C7 C6 H6 119.7
N1 C12 C2 178.6(3)
O1 C3 O2 118.1(3)
O1 C3 C2 125.2(3)
O2 C3 C2 116.7(2)
C8 C7 C6 120.3(3)
C8 C7 H7 119.8
C6 C7 H7 119.8
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C3 1.361(3)
O2 C4 1.377(3)
O1 C3 1.201(3)
C9 C4 1.395(3)
C9 C8 1.402(3)
C9 C1 1.440(3)
C1 C2 1.356(3)
C1 C10 1.498(3)
C4 C5 1.384(4)
C2 C12 1.435(4)
C2 C3 1.454(4)
C8 C7 1.374(4)
C8 H8 0.9500
C10 C11 1.528(4)
C10 H10A 0.9900
C10 H10B 0.9900
C5 C6 1.373(4)
C5 H5 0.9500
N1 C12 1.138(4)
C6 C7 1.380(4)
C6 H6 0.9500
C7 H7 0.9500
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
