#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:38:25 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296693 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160122.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_7160122
loop_
_publ_author_name
'Chandrasekar, Lavanya'
'Hsieh, Yun-Zhen'
'Chou, Hao-Tse'
'Huang, Yu-Chen'
'Liu, Wei-Min'
_publ_section_title
;
 Synthesis of alkynyl cyclopropa[c]coumarins via propargyl
 sulfonium salts as C1 synthons.
;
_journal_issue                   47
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9219
_journal_page_last               9230
_journal_paper_doi               10.1039/d4ob01089b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C19 H11 Cl O3'
_chemical_formula_sum            'C19 H11 Cl O3'
_chemical_formula_weight         322.73
_chemical_name_systematic
(1S,1aR,7bR)-1a-(4-chlorobenzoyl)-1-ethynyl-1a,7b-dihydrocyclopropa[c]chromen-2(1H)-one
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2023-10-15 deposited with the CCDC.	2024-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.1577(3)
_cell_length_b                   19.5983(8)
_cell_length_c                   21.4037(10)
_cell_measurement_reflns_used    8129
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      66.80
_cell_measurement_theta_min      3.06
_cell_volume                     3002.5(2)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9534
_diffrn_reflns_theta_full        66.80
_diffrn_reflns_theta_max         66.80
_diffrn_reflns_theta_min         4.51
_exptl_absorpt_coefficient_mu    2.363
_exptl_absorpt_correction_T_max  0.8155
_exptl_absorpt_correction_T_min  0.2810
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2623
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0787P)²+1.8013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1451
_refine_ls_wR_factor_ref         0.1492
_reflns_number_gt                2367
_reflns_number_total             2623
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob01089b2.cif
_cod_data_source_block           d24730
_cod_depositor_comments
'Adding full bibliography for 7160121--7160122.cif.'
_cod_database_code               7160122
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8743(4) 0.62736(13) 0.64006(11) 0.0495(6) Uani 1 1 d . . .
C2 C 0.8523(3) 0.60748(11) 0.57888(11) 0.0443(6) Uani 1 1 d . . .
H2 H 0.9491 0.5837 0.5577 0.053 Uiso 1 1 calc R . .
C3 C 0.6863(3) 0.62272(10) 0.54877(10) 0.0361(5) Uani 1 1 d . . .
H3 H 0.6693 0.6091 0.5066 0.043 Uiso 1 1 calc R . .
C4 C 0.5431(3) 0.65786(10) 0.57946(10) 0.0360(5) Uani 1 1 d . . .
C5 C 0.5712(4) 0.67870(12) 0.64117(11) 0.0473(6) Uani 1 1 d . . .
H5 H 0.4763 0.7035 0.6623 0.057 Uiso 1 1 calc R . .
C6 C 0.7362(4) 0.66344(14) 0.67152(11) 0.0544(7) Uani 1 1 d . . .
H6 H 0.7551 0.6775 0.7135 0.065 Uiso 1 1 calc R . .
C7 C 0.3654(3) 0.67582(10) 0.54807(10) 0.0377(5) Uani 1 1 d . . .
C8 C 0.3207(3) 0.64229(9) 0.48654(9) 0.0325(5) Uani 1 1 d . . .
C9 C 0.3220(3) 0.56625(10) 0.48536(10) 0.0330(5) Uani 1 1 d . . .
C10 C 0.4284(3) 0.56825(11) 0.37822(10) 0.0362(5) Uani 1 1 d . . .
C11 C 0.4854(3) 0.52658(13) 0.32961(11) 0.0471(6) Uani 1 1 d . . .
H11 H 0.4753 0.4784 0.3328 0.056 Uiso 1 1 calc R . .
C12 C 0.5570(3) 0.55642(15) 0.27636(12) 0.0547(7) Uani 1 1 d . . .
H12 H 0.5952 0.5286 0.2424 0.066 Uiso 1 1 calc R . .
C13 C 0.5735(3) 0.62667(16) 0.27210(12) 0.0548(6) Uani 1 1 d . . .
H13 H 0.6243 0.6469 0.2355 0.066 Uiso 1 1 calc R . .
C14 C 0.5161(3) 0.66732(13) 0.32123(11) 0.0458(5) Uani 1 1 d . . .
H14 H 0.5290 0.7155 0.3184 0.055 Uiso 1 1 calc R . .
C15 C 0.4393(3) 0.63848(11) 0.37491(10) 0.0356(5) Uani 1 1 d . . .
C16 C 0.3695(3) 0.68040(10) 0.42707(10) 0.0357(5) Uani 1 1 d . . .
H16 H 0.4300 0.7260 0.4326 0.043 Uiso 1 1 calc R . .
C17 C 0.1675(3) 0.67517(10) 0.44715(10) 0.0373(5) Uani 1 1 d . . .
H17 H 0.1135 0.7180 0.4650 0.045 Uiso 1 1 calc R . .
C18 C 0.0361(3) 0.63244(12) 0.41477(11) 0.0414(5) Uani 1 1 d . . .
C19 C -0.0700(3) 0.59530(15) 0.38980(13) 0.0557(7) Uani 1 1 d . . .
H19 H -0.1554 0.5654 0.3697 0.067 Uiso 1 1 calc R . .
Cl1 Cl 1.07881(11) 0.60566(4) 0.67930(4) 0.0765(3) Uani 1 1 d . . .
O1 O 0.2617(3) 0.71918(8) 0.56940(9) 0.0554(5) Uani 1 1 d . . .
O2 O 0.2819(2) 0.53237(7) 0.52988(7) 0.0425(4) Uani 1 1 d . . .
O3 O 0.3617(2) 0.53423(7) 0.43107(7) 0.0379(4) Uani 1 1 d . . .
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'
Cl Cl 0.3639 0.7018 '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
C2 C1 C6 121.6(2) . . ?
C2 C1 Cl1 119.1(2) . . ?
C6 C1 Cl1 119.26(19) . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 C7 118.9(2) . . ?
C3 C4 C7 122.23(19) . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O1 C7 C4 121.3(2) . . ?
O1 C7 C8 120.2(2) . . ?
C4 C7 C8 118.37(18) . . ?
C9 C8 C7 116.73(16) . . ?
C9 C8 C16 118.48(17) . . ?
C7 C8 C16 118.03(16) . . ?
C9 C8 C17 114.67(16) . . ?
C7 C8 C17 116.83(17) . . ?
C16 C8 C17 59.61(13) . . ?
O2 C9 O3 118.53(18) . . ?
O2 C9 C8 122.68(19) . . ?
O3 C9 C8 118.72(17) . . ?
C15 C10 C11 122.2(2) . . ?
C15 C10 O3 122.46(18) . . ?
C11 C10 O3 115.33(19) . . ?
C12 C11 C10 118.7(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 119.8(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 118.0(2) . . ?
C10 C15 C16 119.86(18) . . ?
C14 C15 C16 122.2(2) . . ?
C15 C16 C17 120.11(18) . . ?
C15 C16 C8 116.06(17) . . ?
C17 C16 C8 60.50(13) . . ?
C15 C16 H16 116.2 . . ?
C17 C16 H16 116.2 . . ?
C8 C16 H16 116.2 . . ?
C18 C17 C16 121.89(19) . . ?
C18 C17 C8 119.38(17) . . ?
C16 C17 C8 59.89(13) . . ?
C18 C17 H17 114.9 . . ?
C16 C17 H17 114.9 . . ?
C8 C17 H17 114.9 . . ?
C19 C18 C17 177.3(3) . . ?
C18 C19 H19 180.0 . . ?
C9 O3 C10 123.13(16) . . ?
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
C1 C2 1.375(3) . ?
C1 C6 1.390(4) . ?
C1 Cl1 1.741(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(3) . ?
C4 C7 1.481(3) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.217(3) . ?
C7 C8 1.506(3) . ?
C8 C9 1.490(3) . ?
C8 C16 1.517(3) . ?
C8 C17 1.526(3) . ?
C9 O2 1.197(3) . ?
C9 O3 1.351(2) . ?
C10 C15 1.380(3) . ?
C10 C11 1.384(3) . ?
C10 O3 1.397(3) . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.474(3) . ?
C16 C17 1.512(3) . ?
C16 H16 1.0000 . ?
C17 C18 1.437(3) . ?
C17 H17 1.0000 . ?
C18 C19 1.180(4) . ?
C19 H19 0.9500 . ?
