#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:10:35 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/74/4037466.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_4037466
loop_
_publ_author_name
'Han, Sang Hoon'
'Kim, Saegun'
'De, Umasankar'
'Mishra, Neeraj Kumar'
'Park, Jihye'
'Sharma, Satyasheel'
'Kwak, Jong Hwan'
'Han, Sangil'
'Kim, Hyung Sik'
'Kim, In Su'
_publ_section_title
;
 Synthesis of Succinimide-Containing Chromones, Naphthoquinones, and
 Xanthones under Rh(III) Catalysis: Evaluation of Anticancer Activity.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12416
_journal_page_last               12425
_journal_paper_doi               10.1021/acs.joc.6b02577
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C14 H6 N O4'
_chemical_formula_weight         252.20
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 112.056(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.4519(4)
_cell_length_b                   6.8822(3)
_cell_length_c                   10.8607(5)
_cell_measurement_reflns_used    5411
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.60
_cell_volume                     585.51(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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.813
_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  0.0779
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.813
_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            10384
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.560
_diffrn_reflns_theta_min         2.600
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             258
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1319
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.289
_refine_ls_R_factor_all          0.1512
_refine_ls_R_factor_gt           0.1113
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3163
_refine_ls_wR_factor_ref         0.3601
_reflns_Friedel_coverage         0.000
_reflns_number_gt                842
_reflns_number_total             1319
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b02577_si_002.cif
_cod_data_source_block           ye621P21m
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4037466
_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   0.979
_shelx_estimated_absorpt_t_max   0.994
_shelxl_version_number           2013-4
_shelx_hkl_checksum              '46241 &#x00FF;'
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
C1 C 0.3571(5) 0.2500 0.0590(4) 0.0471(10) Uani 1 2 d S T P . .
C2 C 0.1761(6) 0.2500 0.0322(4) 0.0596(12) Uani 1 2 d S T P . .
C3 C 0.0616(7) 0.2500 -0.1075(5) 0.0698(13) Uani 1 2 d S T P . .
H3 H -0.0559 0.2500 -0.1294 0.084 Uiso 1 2 calc R U P . .
C4 C 0.1213(8) 0.2500 -0.2015(5) 0.0811(15) Uani 1 2 d S T P . .
H4 H 0.0430 0.2500 -0.2887 0.097 Uiso 1 2 calc R U P . .
C5 C 0.4063(6) 0.2500 -0.0527(4) 0.0629(12) Uani 1 2 d S T P . .
C6 C 0.5720(7) 0.2500 -0.0412(6) 0.0698(14) Uani 1 2 d S T P . .
H6 H 0.6002 0.2500 -0.1161 0.084 Uiso 1 2 calc R U P . .
C7 C 0.6965(7) 0.2500 0.0840(6) 0.0753(14) Uani 1 2 d S T P . .
H7 H 0.8107 0.2500 0.0939 0.090 Uiso 1 2 calc R U P . .
C8 C 0.6548(5) 0.2500 0.1959(5) 0.0597(12) Uani 1 2 d S T P . .
H8 H 0.7413 0.2500 0.2799 0.072 Uiso 1 2 calc R U P . .
C9 C 0.4881(5) 0.2500 0.1845(4) 0.0501(10) Uani 1 2 d S T P . .
C10 C 0.4526(6) 0.2500 0.3129(4) 0.0736(15) Uani 1 2 d S T P A .
H10 H 0.5644 0.2500 0.3860 0.088 Uiso 1 2 calc R U P . .
O1 O 0.1173(4) 0.2500 0.1211(3) 0.0869(13) Uani 1 2 d S T P . .
O2 O 0.2900(6) 0.2500 -0.1821(3) 0.0859(13) Uani 1 2 d S T P . .
O3 O 0.3692(7) -0.0418(8) 0.3285(5) 0.0691(16) Uani 0.5 1 d . U P A .
C11 C 0.3561(6) 0.0934(12) 0.3404(4) 0.0987(16) Uani 1 1 d . U . . .
N1 N 0.2572(12) 0.2078(12) 0.4134(9) 0.065(4) Uani 0.5 1 d . U P A 1
C13 C 0.1730(5) 0.0315(8) 0.4617(4) 0.1211(17) Uani 0.5 1 d . U P A 1
C12 C 0.2596(12) 0.1087(13) 0.4093(8) 0.0562(19) Uani 0.5 1 d . U P A 2
O4 O 0.1730(5) 0.0315(8) 0.4617(4) 0.1211(17) Uani 0.5 1 d . U P A 2
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
C9 C1 C5 117.0(4) . .
C9 C1 C2 126.0(4) . .
C5 C1 C2 117.0(4) . .
O1 C2 C1 123.1(4) . .
O1 C2 C3 120.3(4) . .
C1 C2 C3 116.6(4) . .
C4 C3 C2 121.0(5) . .
C4 C3 H3 119.5 . .
C2 C3 H3 119.5 . .
C3 C4 O2 124.9(5) . .
C3 C4 H4 117.5 . .
O2 C4 H4 117.5 . .
C6 C5 O2 114.2(4) . .
C6 C5 C1 122.9(4) . .
O2 C5 C1 123.0(4) . .
C5 C6 C7 118.2(4) . .
C5 C6 H6 120.9 . .
C7 C6 H6 120.9 . .
C6 C7 C8 121.0(4) . .
C6 C7 H7 119.5 . .
C8 C7 H7 119.5 . .
C9 C8 C7 120.9(5) . .
C9 C8 H8 119.6 . .
C7 C8 H8 119.6 . .
C8 C9 C1 120.1(4) . .
C8 C9 C10 117.7(4) . .
C1 C9 C10 122.2(3) . .
C11 C10 C11 96.1(6) . 4_565
C11 C10 C9 120.4(3) . .
C11 C10 C9 120.4(3) 4_565 .
C11 C10 H10 106.2 . .
C11 C10 H10 106.2 4_565 .
C9 C10 H10 106.2 . .
C4 O2 C5 117.5(4) . .
O3 C11 C12 106.7(7) . .
O3 C11 C10 126.6(6) . .
C12 C11 C10 125.5(7) . .
O3 C11 N1 132.3(7) . .
C10 C11 N1 100.4(6) . .
O3 C11 N1 147.4(6) . 4_565
C10 C11 N1 85.5(5) . 4_565
N1 C11 N1 15.1(5) . 4_565
N1 N1 C11 120.2(4) 4_565 .
N1 N1 C13 139.7(4) 4_565 .
C11 N1 C13 100.0(6) . .
N1 N1 C11 44.6(3) 4_565 4_565
C11 N1 C11 75.6(6) . 4_565
C13 N1 C11 174.6(6) . 4_565
C11 C12 C12 94.6(5) . 4_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C9 1.397(5) .
C1 C5 1.422(6) .
C1 C2 1.445(6) .
C2 O1 1.241(5) .
C2 C3 1.462(6) .
C3 C4 1.298(8) .
C3 H3 0.9300 .
C4 O2 1.360(8) .
C4 H4 0.9300 .
C5 C6 1.358(7) .
C5 O2 1.380(5) .
C6 C7 1.372(7) .
C6 H6 0.9300 .
C7 C8 1.388(6) .
C7 H7 0.9300 .
C8 C9 1.367(5) .
C8 H8 0.9300 .
C9 C10 1.532(6) .
C10 C11 1.449(7) .
C10 C11 1.449(7) 4_565
C10 H10 0.9800 .
O3 C11 0.952(6) .
C11 C12 1.301(10) .
C11 N1 1.563(11) .
C11 N1 1.923(12) 4_565
N1 N1 0.581(17) 4_565
N1 C13 1.591(10) .
N1 C11 1.923(12) 4_565
C12 C12 1.945(18) 4_565
