#------------------------------------------------------------------------------
#$Date: 2021-09-06 12:34:51 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268588 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/85/7128553.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_7128553
loop_
_publ_author_name
'Xi, Jinhu'
'Wu, Xinjie'
'Huang, Mengmeng'
'Kim, Jung Keun'
'Zhang, Jianye'
'Li, Yabo'
'Wu, Yangjie'
_publ_section_title
;
 A visible-light-induced photocatalyst-free approach for C-3 dicarbonyl
 coumarin production.
;
_journal_issue                   59
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7308
_journal_page_last               7311
_journal_paper_doi               10.1039/d1cc02399c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C17 H10 O4'
_chemical_formula_sum            'C17 H10 O4'
_chemical_formula_weight         278.25
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2020-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-13 deposited with the CCDC.	2021-06-24 downloaded from the CCDC.
;
_cell_angle_alpha                94.814(11)
_cell_angle_beta                 90.307(13)
_cell_angle_gamma                112.254(14)
_cell_formula_units_Z            2
_cell_length_a                   7.1288(11)
_cell_length_b                   7.3017(9)
_cell_length_c                   13.738(2)
_cell_measurement_reflns_used    807
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.1750
_cell_measurement_theta_min      6.4440
_cell_volume                     658.96(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00  90.00   87
  2  ω     57.00 111.00   1.00    1.00    --   36.62 178.00  90.00   54
  3  ω    -35.00 108.00   1.00    1.00    --   36.62   0.00  90.00  143
  4  ω     57.00 111.00   1.00    1.00    --   36.62 178.00 -30.00   54
  5  ω     -4.00  77.00   1.00    1.00    --   36.62 -99.00 -90.00   81
  6  ω     -4.00  77.00   1.00    1.00    --   36.62 -99.00  30.00   81
  7  ω     14.00 107.00   1.00    1.00    --   36.62  37.00  90.00   93
  8  ω     57.00 111.00   1.00    1.00    --   36.62 178.00 -90.00   54
  9  ω     -4.00  77.00   1.00    1.00    --   36.62 -99.00  90.00   81
 10  ω    -32.00  55.00   1.00    1.00    --   36.62 -57.00 120.00   87
 11  ω     14.00 107.00   1.00    1.00    --   36.62  37.00 -30.00   93
 12  ω    106.00 154.00   1.00    3.00    --  108.00 111.00 -60.00   48
 13  ω     79.00 110.00   1.00    3.00    --  108.00-111.00-120.00   31
 14  ω     48.00 122.00   1.00    3.00    --  108.00 -61.00 150.00   74
 15  ω    119.00 165.00   1.00    3.00    --  108.00 111.00 150.00   46
 16  ω     47.00 109.00   1.00    3.00    --  108.00 -94.00 120.00   62
 17  ω    116.00 150.00   1.00    3.00    --  108.00 178.00-180.00   34
 18  ω    114.00 146.00   1.00    3.00    --  108.00 111.00 -90.00   32
 19  ω    143.00 174.00   1.00    3.00    --  108.00  61.00   0.00   31
 20  ω     94.00 121.00   1.00    3.00    --  108.00  61.00   0.00   27
 21  ω     70.00  98.00   1.00    3.00    --  108.00 178.00-180.00   28
 22  ω     43.00 114.00   1.00    3.00    --  108.00 -45.00   0.00   71
 23  ω     73.00 103.00   1.00    3.00    --  108.00-111.00   0.00   30
 24  ω    102.00 127.00   1.00    3.00    --  108.00 111.00  60.00   25
 25  ω    147.00 176.00   1.00    3.00    --  108.00 111.00  60.00   29
 26  ω     38.00  65.00   1.00    3.00    --  108.00-111.00   0.00   27
 27  ω     39.00 148.00   1.00    3.00    --  108.00 -15.00-180.00  109
 28  ω     50.00 128.00   1.00    3.00    --  108.00 -61.00-120.00   78
 29  ω     90.00 176.00   1.00    3.00    --  108.00  30.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0601985000
_diffrn_orient_matrix_UB_12      -0.1479047000
_diffrn_orient_matrix_UB_13      0.0788248000
_diffrn_orient_matrix_UB_21      0.1455523000
_diffrn_orient_matrix_UB_22      0.1605645000
_diffrn_orient_matrix_UB_23      0.0748512000
_diffrn_orient_matrix_UB_31      -0.1726269000
_diffrn_orient_matrix_UB_32      0.0690217000
_diffrn_orient_matrix_UB_33      0.0294833000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4663
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.059
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         6.472
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       octahedral
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0638
_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)+(0.1090P)²+0.0550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1804
_refine_ls_wR_factor_ref         0.2205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1404
_reflns_number_total             2352
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02399c2.cif
_cod_data_source_block           202010208
_cod_depositor_comments
'Adding full bibliography for 7128552--7128554.cif.'
_cod_original_cell_volume        658.95(18)
_cod_database_code               7128553
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N4
_chemical_oxdiff_usercomment     r
_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_max   0.967
_shelx_estimated_absorpt_t_min   0.838
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.397
_oxdiff_exptl_absorpt_empirical_full_min 0.609
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2239(3) 0.2084(3) 0.51657(17) 0.0668(6) Uani 1 1 d . . . . .
C1 C 0.7589(5) 0.2891(5) 0.4822(3) 0.0666(9) Uani 1 1 d . . . . .
H1 H 0.8733 0.2954 0.5174 0.080 Uiso 1 1 calc R . . . .
O2 O 0.0304(3) 0.1478(4) 0.6427(2) 0.0824(8) Uani 1 1 d . . . . .
C2 C 0.7705(5) 0.3167(5) 0.3857(3) 0.0709(9) Uani 1 1 d . . . . .
H2 H 0.8931 0.3430 0.3553 0.085 Uiso 1 1 calc R . . . .
O3 O 0.4871(4) 0.1701(4) 0.8308(2) 0.0901(9) Uani 1 1 d . . . . .
C3 C 0.5996(6) 0.3060(5) 0.3315(3) 0.0732(9) Uani 1 1 d . . . . .
H3 H 0.6089 0.3254 0.2654 0.088 Uiso 1 1 calc R . . . .
C4 C 0.4169(5) 0.2665(5) 0.3760(3) 0.0674(9) Uani 1 1 d . . . . .
H4 H 0.3019 0.2564 0.3400 0.081 Uiso 1 1 calc R . . . .
O4 O 0.1664(4) 0.3587(4) 0.8458(2) 0.0884(8) Uani 1 1 d . . . . .
C5 C 0.4075(4) 0.2425(4) 0.4735(3) 0.0594(8) Uani 1 1 d . . . . .
C6 C 0.5758(4) 0.2512(4) 0.5295(2) 0.0575(8) Uani 1 1 d . . . . .
C7 C 0.5546(4) 0.2282(4) 0.6306(3) 0.0585(8) Uani 1 1 d . . . . .
H7 H 0.6655 0.2340 0.6685 0.070 Uiso 1 1 calc R . . . .
C8 C 0.3758(4) 0.1980(4) 0.6732(3) 0.0589(8) Uani 1 1 d . . . . .
C9 C 0.1978(5) 0.1821(5) 0.6131(3) 0.0623(8) Uani 1 1 d . . . . .
C10 C 0.3542(5) 0.1806(5) 0.7785(3) 0.0653(9) Uani 1 1 d . . . . .
C11 C 0.1662(5) 0.1926(5) 0.8286(3) 0.0667(9) Uani 1 1 d . . . . .
C12 C 0.0089(5) 0.0089(5) 0.8575(2) 0.0630(8) Uani 1 1 d . . . . .
C13 C -0.1711(5) 0.0151(6) 0.8915(3) 0.0765(10) Uani 1 1 d . . . . .
H13 H -0.1898 0.1348 0.8974 0.092 Uiso 1 1 calc R . . . .
C14 C -0.3229(6) -0.1560(7) 0.9165(3) 0.0876(12) Uani 1 1 d . . . . .
H14 H -0.4445 -0.1521 0.9386 0.105 Uiso 1 1 calc R . . . .
C15 C -0.2939(7) -0.3328(7) 0.9087(3) 0.0923(13) Uani 1 1 d . . . . .
H15 H -0.3959 -0.4482 0.9259 0.111 Uiso 1 1 calc R . . . .
C16 C -0.1154(7) -0.3389(6) 0.8758(3) 0.0943(13) Uani 1 1 d . . . . .
H16 H -0.0964 -0.4585 0.8710 0.113 Uiso 1 1 calc R . . . .
C17 C 0.0361(6) -0.1695(6) 0.8500(3) 0.0787(10) Uani 1 1 d . . . . .
H17 H 0.1569 -0.1747 0.8274 0.094 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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
C9 O1 C5 122.5(2) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.6(3) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
O1 C5 C6 120.1(3) . . ?
C4 C5 O1 117.7(3) . . ?
C4 C5 C6 122.2(3) . . ?
C1 C6 C7 123.6(3) . . ?
C5 C6 C1 117.6(3) . . ?
C5 C6 C7 118.7(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 C10 121.6(3) . . ?
C10 C8 C9 118.7(3) . . ?
O1 C9 C8 117.7(3) . . ?
O2 C9 O1 117.2(3) . . ?
O2 C9 C8 125.1(3) . . ?
O3 C10 C8 122.4(3) . . ?
O3 C10 C11 117.1(3) . . ?
C8 C10 C11 120.3(3) . . ?
O4 C11 C10 115.8(3) . . ?
O4 C11 C12 125.2(3) . . ?
C12 C11 C10 119.0(3) . . ?
C13 C12 C11 119.0(3) . . ?
C17 C12 C11 121.5(3) . . ?
C17 C12 C13 119.5(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.9(4) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 120.0 . . ?
C16 C17 C12 120.0(4) . . ?
C16 C17 H17 120.0 . . ?
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 C5 1.382(4) . ?
O1 C9 1.359(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.356(5) . ?
C1 C6 1.403(4) . ?
O2 C9 1.204(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(5) . ?
O3 C10 1.215(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(5) . ?
O4 C11 1.216(4) . ?
C5 C6 1.400(4) . ?
C6 C7 1.415(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.354(4) . ?
C8 C9 1.472(4) . ?
C8 C10 1.467(5) . ?
C10 C11 1.538(4) . ?
C11 C12 1.473(5) . ?
C12 C13 1.383(5) . ?
C12 C17 1.383(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.368(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(5) . ?
C17 H17 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
O1 C5 C6 C1 -179.1(3) . . . . ?
O1 C5 C6 C7 -1.2(4) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C1 C6 C7 C8 177.9(3) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C2 C1 C6 C7 -177.6(3) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
O3 C10 C11 O4 96.7(4) . . . . ?
O3 C10 C11 C12 -79.4(4) . . . . ?
C3 C4 C5 O1 178.3(3) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C4 C5 C6 C7 178.9(3) . . . . ?
O4 C11 C12 C13 12.1(5) . . . . ?
O4 C11 C12 C17 -169.0(4) . . . . ?
C5 O1 C9 O2 -178.0(3) . . . . ?
C5 O1 C9 C8 2.2(4) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C6 C1 C2 C3 -0.6(5) . . . . ?
C6 C7 C8 C9 2.0(4) . . . . ?
C6 C7 C8 C10 -178.0(3) . . . . ?
C7 C8 C9 O1 -3.2(4) . . . . ?
C7 C8 C9 O2 177.0(3) . . . . ?
C7 C8 C10 O3 -8.4(5) . . . . ?
C7 C8 C10 C11 166.5(3) . . . . ?
C8 C10 C11 O4 -78.4(4) . . . . ?
C8 C10 C11 C12 105.4(4) . . . . ?
C9 O1 C5 C4 179.9(3) . . . . ?
C9 O1 C5 C6 0.0(4) . . . . ?
C9 C8 C10 O3 171.6(3) . . . . ?
C9 C8 C10 C11 -13.5(4) . . . . ?
C10 C8 C9 O1 176.8(3) . . . . ?
C10 C8 C9 O2 -3.0(5) . . . . ?
C10 C11 C12 C13 -172.1(3) . . . . ?
C10 C11 C12 C17 6.8(5) . . . . ?
C11 C12 C13 C14 178.2(4) . . . . ?
C11 C12 C17 C16 -178.7(4) . . . . ?
C12 C13 C14 C15 0.8(6) . . . . ?
C13 C12 C17 C16 0.2(6) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
C14 C15 C16 C17 -0.2(7) . . . . ?
C15 C16 C17 C12 0.3(7) . . . . ?
C17 C12 C13 C14 -0.7(5) . . . . ?
