#------------------------------------------------------------------------------
#$Date: 2022-06-06 05:04:59 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275825 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158579.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_7158579
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         'C17 H12 O3'
_chemical_formula_sum            'C17 H12 O3'
_chemical_formula_weight         264.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-10-06
_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                90
_cell_angle_beta                 94.036(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3812(7)
_cell_length_b                   5.5547(3)
_cell_length_c                   18.6375(10)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.19
_cell_volume                     1278.59(12)
_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      300.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0583
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            38499
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.043
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1060 before and 0.0723 after correction. The Ratio of minimum to maximum transmission is 0.9273. 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    1.373
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.784
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.287
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.287
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0829
_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)+(0.1197P)²+0.1518P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1912
_refine_ls_wR_factor_ref         0.1975
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1931
_reflns_number_total             2249
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00438k4.cif
_cod_data_source_block           dbr006_0m_a
_cod_depositor_comments
'Adding full bibliography for 7158576--7158579.cif.'
_cod_database_code               7158579
_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   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C13(H13), C16(H16), C15(H15), C3(H3), C4(H4), C1(H1A), C2(H2)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.53731(13) 0.8927(3) 0.38735(7) 0.0570(5) Uani 1 1 d . . . . .
H1 H 0.535797 0.951024 0.427675 0.086 Uiso 1 1 calc GR . . . .
O2 O 0.36385(11) 0.2600(2) 0.25882(7) 0.0494(4) Uani 1 1 d . . . . .
O3 O 0.42455(13) 0.7764(3) 0.49893(8) 0.0600(5) Uani 1 1 d . . . . .
C6 C 0.53046(15) 0.6064(3) 0.26027(10) 0.0394(5) Uani 1 1 d . . . . .
C12 C 0.37923(14) 0.3741(3) 0.31477(9) 0.0384(5) Uani 1 1 d . . . . .
C7 C 0.45947(15) 0.5698(3) 0.32071(10) 0.0393(5) Uani 1 1 d . . . . .
C10 C 0.33047(15) 0.4523(3) 0.44092(9) 0.0417(5) Uani 1 1 d . . . . .
C5 C 0.60912(16) 0.4351(4) 0.24889(10) 0.0462(5) Uani 1 1 d . . . . .
H5 H 0.614955 0.298695 0.277849 0.055 Uiso 1 1 calc R . . . .
C13 C 0.24110(15) 0.1309(4) 0.37316(10) 0.0447(5) Uani 1 1 d . . . . .
H13 H 0.231705 0.041825 0.330926 0.054 Uiso 1 1 calc R . . . .
C8 C 0.46875(14) 0.7070(4) 0.38081(10) 0.0433(5) Uani 1 1 d . . . . .
C14 C 0.18053(16) 0.0735(4) 0.43113(11) 0.0479(5) Uani 1 1 d . . . . .
C16 C 0.27182(18) 0.3927(4) 0.49942(11) 0.0525(6) Uani 1 1 d . . . . .
H16 H 0.282740 0.477759 0.542291 0.063 Uiso 1 1 calc R . . . .
C9 C 0.40694(15) 0.6538(4) 0.44477(9) 0.0440(5) Uani 1 1 d . . . . .
C15 C 0.19754(17) 0.2075(4) 0.49385(11) 0.0534(6) Uani 1 1 d . . . . .
H15 H 0.157852 0.171500 0.533024 0.064 Uiso 1 1 calc R . . . .
C3 C 0.66968(18) 0.6653(4) 0.15134(11) 0.0551(6) Uani 1 1 d . . . . .
H3 H 0.716795 0.686432 0.115132 0.066 Uiso 1 1 calc R . . . .
C11 C 0.31492(14) 0.3181(3) 0.37747(9) 0.0397(5) Uani 1 1 d . . . . .
C4 C 0.67884(17) 0.4657(4) 0.19482(12) 0.0524(6) Uani 1 1 d . . . . .
H4 H 0.731906 0.351146 0.187898 0.063 Uiso 1 1 calc R . . . .
C1 C 0.52171(18) 0.8057(4) 0.21622(11) 0.0521(6) Uani 1 1 d . . . . .
H1A H 0.469306 0.921606 0.223271 0.063 Uiso 1 1 calc R . . . .
C17 C 0.09896(18) -0.1270(4) 0.42473(13) 0.0598(6) Uani 1 1 d . . . . .
H17A H 0.032613 -0.068294 0.401283 0.090 Uiso 1 1 calc GR . . . .
H17B H 0.085640 -0.184843 0.471834 0.090 Uiso 1 1 calc GR . . . .
H17C H 0.126517 -0.255930 0.396983 0.090 Uiso 1 1 calc GR . . . .
C2 C 0.5909(2) 0.8339(4) 0.16133(12) 0.0598(6) Uani 1 1 d . . . . .
H2 H 0.583941 0.967372 0.131237 0.072 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 0.0033 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
C5 C6 C7 118.64(17) . . ?
C1 C6 C7 122.26(17) . . ?
C1 C6 C5 119.09(18) . . ?
O2 C12 C7 120.71(17) . . ?
O2 C12 C11 119.98(17) . . ?
C7 C12 C11 119.31(15) . . ?
C12 C7 C6 118.33(15) . . ?
C8 C7 C6 121.91(17) . . ?
C8 C7 C12 119.74(16) . . ?
C16 C10 C9 120.98(17) . . ?
C16 C10 C11 119.12(19) . . ?
C11 C10 C9 119.90(16) . . ?
C4 C5 C6 120.51(19) . . ?
C11 C13 C14 121.06(18) . . ?
O1 C8 C7 121.78(17) . . ?
O1 C8 C9 116.03(15) . . ?
C7 C8 C9 122.13(17) . . ?
C13 C14 C17 120.20(19) . . ?
C15 C14 C13 118.12(19) . . ?
C15 C14 C17 121.68(18) . . ?
C15 C16 C10 120.05(19) . . ?
O3 C9 C10 122.85(18) . . ?
O3 C9 C8 118.51(18) . . ?
C10 C9 C8 118.61(15) . . ?
C16 C15 C14 121.59(18) . . ?
C4 C3 C2 120.02(19) . . ?
C10 C11 C12 120.08(17) . . ?
C13 C11 C12 119.86(16) . . ?
C13 C11 C10 120.05(17) . . ?
C3 C4 C5 120.0(2) . . ?
C6 C1 C2 120.18(19) . . ?
C3 C2 C1 120.2(2) . . ?
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 C8 1.336(2) . ?
O2 C12 1.224(2) . ?
O3 C9 1.225(2) . ?
C6 C7 1.491(3) . ?
C6 C5 1.388(3) . ?
C6 C1 1.378(3) . ?
C12 C7 1.472(3) . ?
C12 C11 1.493(3) . ?
C7 C8 1.353(2) . ?
C10 C16 1.392(3) . ?
C10 C9 1.464(3) . ?
C10 C11 1.400(2) . ?
C5 C4 1.383(3) . ?
C13 C14 1.395(3) . ?
C13 C11 1.383(3) . ?
C8 C9 1.491(3) . ?
C14 C15 1.390(3) . ?
C14 C17 1.502(3) . ?
C16 C15 1.379(3) . ?
C3 C4 1.374(3) . ?
C3 C2 1.374(3) . ?
C1 C2 1.389(3) . ?
