#------------------------------------------------------------------------------
#$Date: 2022-06-06 05:04:59 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275825 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158576.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_7158576
loop_
_publ_author_name
'Krishna, Anugam V.'
'Ramachary, Dhevalapally B.'
_publ_section_title
;
 The seven-step, one-pot regioselective synthesis of biologically
 important 3-aryllawsones: scope and applications.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3948
_journal_page_last               3954
_journal_paper_doi               10.1039/d2ob00438k
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C18 H14 O3'
_chemical_formula_sum            'C18 H14 O3'
_chemical_formula_weight         278.29
_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_date             2021-09-30
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2021-12-09 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                102.226(2)
_cell_angle_beta                 92.692(2)
_cell_angle_gamma                90.534(2)
_cell_formula_units_Z            2
_cell_length_a                   5.5942(3)
_cell_length_b                   10.5681(6)
_cell_length_c                   11.9447(6)
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.34
_cell_volume                     689.26(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0741
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41553
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_min         1.747
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6719
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1084 before and 0.0842 after correction. The Ratio of minimum to maximum transmission is 0.9012. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       plate
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0745
_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)+(0.1214P)²+0.0219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1827
_refine_ls_wR_factor_ref         0.1981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2214
_reflns_number_total             3181
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00438k4.cif
_cod_data_source_block           dbr005_0m_a
_cod_depositor_comments
'Adding full bibliography for 7158576--7158579.cif.'
_cod_database_code               7158576
_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.
;
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3A), C2(H2), C17(H17), C16(H16), C13(H13), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.76851(19) 0.47218(11) 0.56293(10) 0.0452(4) Uani 1 1 d . . . . .
O3 O 0.91754(19) 0.31900(11) 0.37122(10) 0.0441(3) Uani 1 1 d . . . . .
H3 H 0.969506 0.388923 0.408356 0.066 Uiso 1 1 calc GR . . . .
O2 O 0.2950(2) 0.02847(12) 0.39253(12) 0.0596(4) Uani 1 1 d . . . . .
C9 C 0.7282(3) 0.28142(14) 0.42217(13) 0.0346(4) Uani 1 1 d . . . . .
C5 C 0.4525(3) 0.33112(15) 0.58765(13) 0.0342(4) Uani 1 1 d . . . . .
C8 C 0.6094(3) 0.16986(14) 0.37579(13) 0.0356(4) Uani 1 1 d . . . . .
C10 C 0.6576(2) 0.37017(14) 0.52855(13) 0.0335(4) Uani 1 1 d . . . . .
C4 C 0.3326(3) 0.21421(15) 0.54292(13) 0.0354(4) Uani 1 1 d . . . . .
C7 C 0.4057(3) 0.12916(15) 0.43350(14) 0.0381(4) Uani 1 1 d . . . . .
C12 C 0.6280(3) 0.14198(14) 0.16005(14) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.1779(3) 0.38018(18) 0.74071(14) 0.0461(4) Uani 1 1 d . . . . .
C6 C 0.3756(3) 0.41371(16) 0.68577(14) 0.0410(4) Uani 1 1 d . . . . .
H6 H 0.456890 0.491794 0.714772 0.049 Uiso 1 1 calc R . . . .
C3 C 0.1406(3) 0.17853(17) 0.59881(15) 0.0433(4) Uani 1 1 d . . . . .
H3A H 0.061978 0.099407 0.570891 0.052 Uiso 1 1 calc R . . . .
C11 C 0.6821(3) 0.08606(16) 0.26475(14) 0.0426(4) Uani 1 1 d . . . . .
H11A H 0.600522 0.002645 0.254030 0.051 Uiso 1 1 calc R . . . .
H11B H 0.852685 0.071374 0.270748 0.051 Uiso 1 1 calc R . . . .
C2 C 0.0648(3) 0.26136(18) 0.69714(15) 0.0475(5) Uani 1 1 d . . . . .
H2 H -0.064329 0.236440 0.734345 0.057 Uiso 1 1 calc R . . . .
C17 C 0.7785(4) 0.1188(2) 0.07067(17) 0.0616(6) Uani 1 1 d . . . . .
H17 H 0.917537 0.072999 0.077609 0.074 Uiso 1 1 calc R . . . .
C16 C 0.7292(4) 0.1616(2) -0.02889(18) 0.0726(6) Uani 1 1 d . . . . .
H16 H 0.832123 0.142351 -0.088821 0.087 Uiso 1 1 calc R . . . .
C13 C 0.4276(3) 0.2129(2) 0.14788(17) 0.0598(5) Uani 1 1 d . . . . .
H13 H 0.323228 0.231295 0.207275 0.072 Uiso 1 1 calc R . . . .
C15 C 0.5314(4) 0.2316(2) -0.03990(18) 0.0669(6) Uani 1 1 d . . . . .
H15 H 0.499145 0.261968 -0.106545 0.080 Uiso 1 1 calc R . . . .
C14 C 0.3791(4) 0.2572(2) 0.0484(2) 0.0731(7) Uani 1 1 d . . . . .
H14 H 0.242150 0.304703 0.041362 0.088 Uiso 1 1 calc R . . . .
C18 C 0.0856(4) 0.4721(2) 0.84279(19) 0.0703(6) Uani 1 1 d . . . . .
H18A H 0.205147 0.485732 0.904713 0.105 Uiso 1 1 calc GR . . . .
H18B H -0.056942 0.435922 0.866272 0.105 Uiso 1 1 calc GR . . . .
H18C H 0.049750 0.553270 0.822505 0.105 Uiso 1 1 calc GR . . . .
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'
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
O3 C9 C8 120.49(14) . . ?
O3 C9 C10 116.46(13) . . ?
C8 C9 C10 123.04(14) . . ?
C4 C5 C10 119.76(14) . . ?
C4 C5 C6 120.52(14) . . ?
C6 C5 C10 119.69(14) . . ?
C9 C8 C7 119.81(14) . . ?
C9 C8 C11 120.91(14) . . ?
C7 C8 C11 119.29(14) . . ?
O1 C10 C9 119.24(13) . . ?
O1 C10 C5 122.83(14) . . ?
C5 C10 C9 117.92(13) . . ?
C5 C4 C7 120.57(13) . . ?
C3 C4 C5 119.34(15) . . ?
C3 C4 C7 120.06(15) . . ?
O2 C7 C8 120.77(15) . . ?
O2 C7 C4 120.37(14) . . ?
C8 C7 C4 118.84(14) . . ?
C17 C12 C11 119.86(15) . . ?
C13 C12 C11 122.67(15) . . ?
C13 C12 C17 117.43(16) . . ?
C6 C1 C18 120.75(17) . . ?
C2 C1 C6 118.31(16) . . ?
C2 C1 C18 120.92(17) . . ?
C1 C6 C5 120.48(16) . . ?
C4 C3 C2 119.87(16) . . ?
C8 C11 C12 114.49(13) . . ?
C1 C2 C3 121.43(15) . . ?
C12 C17 C16 121.83(18) . . ?
C15 C16 C17 120.24(19) . . ?
C12 C13 C14 120.83(18) . . ?
C16 C15 C14 119.18(19) . . ?
C15 C14 C13 120.47(19) . . ?
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 C10 1.2215(18) . ?
O3 C9 1.3433(17) . ?
O2 C7 1.2222(19) . ?
C9 C8 1.347(2) . ?
C9 C10 1.483(2) . ?
C5 C10 1.475(2) . ?
C5 C4 1.390(2) . ?
C5 C6 1.393(2) . ?
C8 C7 1.466(2) . ?
C8 C11 1.506(2) . ?
C4 C7 1.498(2) . ?
C4 C3 1.381(2) . ?
C12 C11 1.512(2) . ?
C12 C17 1.373(3) . ?
C12 C13 1.373(2) . ?
C1 C6 1.392(2) . ?
C1 C2 1.388(3) . ?
C1 C18 1.505(3) . ?
C3 C2 1.394(3) . ?
C17 C16 1.376(3) . ?
C16 C15 1.353(3) . ?
C13 C14 1.383(3) . ?
C15 C14 1.371(3) . ?
