#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:17:45 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298008 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134047.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_7134047
loop_
_publ_author_name
'Vinodkumar, Ramavath'
'Nakate, Ashwini K.'
'Krishna, Gamidi Rama'
'Kontham, Ravindar'
_publ_section_title
;
 AgOTf-catalyzed cascade annulation of 5-hexyn-1-ols and aldehydes:
 enabling the diastereoselective synthesis of [6,6,6]-trioxa-fused ketals
 and hexahydro-2H-chromenes.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              973
_journal_page_last               976
_journal_paper_doi               10.1039/d4cc05546b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C19 H25 Cl O3'
_chemical_formula_sum            'C19 H25 Cl O3'
_chemical_formula_weight         336.84
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-02-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-20 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.719(3)
_cell_length_b                   12.729(2)
_cell_length_c                   8.8925(17)
_cell_measurement_reflns_used    5838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.79
_cell_volume                     1666.1(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_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  0.1605
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            54108
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.990
_diffrn_reflns_theta_min         2.676
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1352 before and 0.0961 after correction.
The Ratio of minimum to maximum transmission is 0.8778.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       Plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.949
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0903
_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)+(0.0638P)²+8.3943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2061
_refine_ls_wR_factor_ref         0.2138
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1612
_reflns_number_total             1885
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05546b2.cif
_cod_data_source_block           5as
_cod_depositor_comments
'Adding full bibliography for 7134046--7134049.cif.'
_cod_database_code               7134047
_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.
;
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
C1 C 0.5380(4) 0.750000 0.1959(7) 0.0211(12) Uani 1 2 d S T P . .
C2 C 0.4436(4) 0.750000 0.1907(6) 0.0190(11) Uani 1 2 d S T P . .
H2 H 0.411470 0.750000 0.098003 0.023 Uiso 1 2 calc R U P . .
C3 C 0.3982(4) 0.750000 0.3292(6) 0.0191(11) Uani 1 2 d S T P . .
H3 H 0.333677 0.750000 0.329945 0.023 Uiso 1 2 calc R U P . .
C4 C 0.4443(4) 0.750000 0.4656(6) 0.0156(11) Uani 1 2 d S T P . .
C5 C 0.5377(4) 0.750000 0.4623(7) 0.0187(11) Uani 1 2 d S T P . .
H5 H 0.570461 0.750000 0.554286 0.022 Uiso 1 2 calc R U P . .
C6 C 0.5851(4) 0.750000 0.3275(7) 0.0210(12) Uani 1 2 d S T P . .
H6 H 0.649605 0.750000 0.327077 0.025 Uiso 1 2 calc R U P . .
C7 C 0.3919(3) 0.750000 0.6126(6) 0.0133(10) Uani 1 2 d S T P . .
H7 H 0.437117 0.750000 0.696523 0.016 Uiso 1 2 calc R U P . .
C8 C 0.3334(2) 0.6506(3) 0.6282(4) 0.0134(7) Uani 1 1 d . . . . .
H8 H 0.290086 0.648824 0.541618 0.016 Uiso 1 1 calc R U . . .
C9 C 0.3904(3) 0.5498(3) 0.6228(4) 0.0154(8) Uani 1 1 d . . . . .
H9A H 0.349640 0.488299 0.613682 0.018 Uiso 1 1 calc R U . . .
H9B H 0.430230 0.551409 0.533050 0.018 Uiso 1 1 calc R U . . .
C10 C 0.4486(3) 0.5385(3) 0.7639(5) 0.0210(9) Uani 1 1 d . . . . .
H10A H 0.480314 0.469890 0.762892 0.025 Uiso 1 1 calc R U . . .
H10B H 0.494942 0.594813 0.766944 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3873(3) 0.5459(3) 0.9019(4) 0.0204(8) Uani 1 1 d . . . . .
H11A H 0.346223 0.484354 0.904355 0.024 Uiso 1 1 calc R U . . .
H11B H 0.425205 0.544127 0.993868 0.024 Uiso 1 1 calc R U . . .
C12 C 0.2772(2) 0.6526(3) 0.7738(4) 0.0150(8) Uani 1 1 d . . . . .
C13 C 0.2009(3) 0.5729(3) 0.7715(4) 0.0190(8) Uani 1 1 d . . . . .
H13A H 0.164493 0.579890 0.863180 0.028 Uiso 1 1 calc R U . . .
H13B H 0.226517 0.501872 0.766353 0.028 Uiso 1 1 calc R U . . .
H13C H 0.162334 0.585183 0.683411 0.028 Uiso 1 1 calc R U . . .
Cl1 Cl 0.59775(11) 0.750000 0.02351(17) 0.0276(4) Uani 1 2 d S T P . .
O1 O 0.33468(18) 0.6395(2) 0.9011(3) 0.0166(6) Uani 1 1 d . . . . .
O2 O 0.2317(2) 0.750000 0.7937(4) 0.0163(8) Uani 1 2 d S T P . .
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'
Cl Cl 0.1484 0.1585 '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
C2 C1 Cl1 117.9(5) . . ?
C6 C1 C2 122.5(5) . . ?
C6 C1 Cl1 119.6(5) . . ?
C1 C2 H2 121.7 . . ?
C1 C2 C3 116.5(5) . . ?
C3 C2 H2 121.7 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.3(5) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C7 120.2(5) . . ?
C5 C4 C3 118.0(5) . . ?
C5 C4 C7 121.8(5) . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.4(6) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.2(5) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C4 C7 H7 107.8 . . ?
C4 C7 C8 111.3(3) . . ?
C4 C7 C8 111.3(3) . 7_575 ?
C8 C7 H7 107.8 . . ?
C8 C7 H7 107.8 7_575 . ?
C8 C7 C8 110.8(4) 7_575 . ?
C7 C8 H8 107.8 . . ?
C9 C8 C7 112.3(3) . . ?
C9 C8 H8 107.8 . . ?
C9 C8 C12 109.6(3) . . ?
C12 C8 C7 111.3(3) . . ?
C12 C8 H8 107.8 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.1(3) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 C9 108.9(3) . . ?
C11 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
O1 C11 C10 111.7(3) . . ?
O1 C11 H11A 109.3 . . ?
O1 C11 H11B 109.3 . . ?
C13 C12 C8 112.1(3) . . ?
O1 C12 C8 110.4(3) . . ?
O1 C12 C13 111.9(3) . . ?
O2 C12 C8 111.9(3) . . ?
O2 C12 C13 103.7(3) . . ?
O2 C12 O1 106.5(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 O1 C12 115.2(3) . . ?
C12 O2 C12 121.6(4) . 7_575 ?
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 1.391(9) . ?
C1 C6 1.359(9) . ?
C1 Cl1 1.767(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(8) . ?
C4 C5 1.375(8) . ?
C4 C7 1.518(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(8) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.537(4) . ?
C7 C8 1.537(4) 7_575 ?
C8 H8 1.0000 . ?
C8 C9 1.533(5) . ?
C8 C12 1.536(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.526(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.526(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 O1 1.421(5) . ?
C12 C13 1.514(5) . ?
C12 O1 1.423(4) . ?
C12 O2 1.420(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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
C1 C2 C3 C4 0.000(1) . . . . ?
C2 C1 C6 C5 0.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C2 C3 C4 C7 180.000(1) . . . . ?
C3 C4 C5 C6 0.000(1) . . . . ?
C3 C4 C7 C8 -62.1(3) . . . 7_575 ?
C3 C4 C7 C8 62.1(3) . . . . ?
C4 C5 C6 C1 0.000(1) . . . . ?
C4 C7 C8 C9 59.1(5) . . . . ?
C4 C7 C8 C12 -177.6(3) . . . . ?
C5 C4 C7 C8 -117.9(3) . . . . ?
C5 C4 C7 C8 117.9(3) . . . 7_575 ?
C6 C1 C2 C3 0.000(1) . . . . ?
C7 C4 C5 C6 180.000(1) . . . . ?
C7 C8 C9 C10 69.8(4) . . . . ?
C7 C8 C12 C13 164.0(3) . . . . ?
C7 C8 C12 O1 -70.5(4) . . . . ?
C7 C8 C12 O2 47.9(4) . . . . ?
C8 C7 C8 C9 -176.5(3) 7_575 . . . ?
C8 C7 C8 C12 -53.2(5) 7_575 . . . ?
C8 C9 C10 C11 54.1(4) . . . . ?
C8 C12 O1 C11 -57.8(4) . . . . ?
C8 C12 O2 C12 -46.9(5) . . . 7_575 ?
C9 C8 C12 C13 -71.2(4) . . . . ?
C9 C8 C12 O1 54.3(4) . . . . ?
C9 C8 C12 O2 172.7(3) . . . . ?
C9 C10 C11 O1 -54.6(4) . . . . ?
C10 C11 O1 C12 58.5(4) . . . . ?
C12 C8 C9 C10 -54.5(4) . . . . ?
C13 C12 O1 C11 67.9(4) . . . . ?
C13 C12 O2 C12 -168.0(3) . . . 7_575 ?
Cl1 C1 C2 C3 180.000(0) . . . . ?
Cl1 C1 C6 C5 180.000(1) . . . . ?
O1 C12 O2 C12 73.8(5) . . . 7_575 ?
O2 C12 O1 C11 -179.5(3) . . . . ?
