#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:08:27 +0200 (Tue, 04 Mar 2025) $
#$Revision: 297988 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/40/7134030.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_7134030
loop_
_publ_author_name
'Cariello, Guilherme'
'Gallo, Rafael D. C.'
'Deflon, Victor M.'
'Cormanich, Rodrigo A.'
'Jurberg, Igor D.'
_publ_section_title
;
 Visible light-mediated formal alkylation and [4+1]-cycloaddition
 strategies of silyl enol ethers with aryldiazoacetates.
;
_journal_issue                   10
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2044
_journal_page_last               2047
_journal_paper_doi               10.1039/d4cc05451b
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C17 H15 Cl O3'
_chemical_formula_weight         302.74
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-09-16 deposited with the CCDC.	2024-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8616(7)
_cell_length_b                   17.3612(11)
_cell_length_c                   8.0514(4)
_cell_measurement_reflns_used    4336
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.26
_cell_measurement_theta_min      2.21
_cell_volume                     1518.26(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0863
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22340
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_min         2.212
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 802 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0490
_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)+(0.0298P)²+0.5240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2274
_reflns_number_total             3096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05451b2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7134030.cif.'
_cod_database_code               7134030
_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_min   0.882
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 0.5404(4) 0.1197(2) 0.3288(6) 0.0575(11) Uani 1 1 d . . . . .
H1 H 0.620691 0.105368 0.354266 0.069 Uiso 1 1 calc R U . . .
C2 C 0.4664(4) 0.0688(3) 0.2429(6) 0.0598(11) Uani 1 1 d . . . . .
H2 H 0.496636 0.020923 0.210842 0.072 Uiso 1 1 calc R U . . .
C3 C 0.3478(4) 0.0895(2) 0.2053(5) 0.0544(11) Uani 1 1 d . . . . .
C4 C 0.3031(4) 0.1604(2) 0.2498(6) 0.0594(12) Uani 1 1 d . . . . .
H4 H 0.223356 0.174816 0.221179 0.071 Uiso 1 1 calc R U . . .
C5 C 0.3781(4) 0.2104(2) 0.3378(7) 0.0543(11) Uani 1 1 d . . . . .
H5 H 0.346938 0.257919 0.370820 0.065 Uiso 1 1 calc R U . . .
C6 C 0.4985(4) 0.1914(2) 0.3780(5) 0.0458(10) Uani 1 1 d . . . . .
C7 C 0.5801(4) 0.2440(2) 0.4818(5) 0.0459(10) Uani 1 1 d . . . . .
H7 H 0.666328 0.229875 0.462974 0.055 Uiso 1 1 calc R U . . .
C8 C 0.5642(4) 0.3294(2) 0.4432(6) 0.0521(11) Uani 1 1 d . . . . .
H8A H 0.578914 0.337986 0.325796 0.062 Uiso 1 1 calc R U . . .
H8B H 0.480162 0.344556 0.467305 0.062 Uiso 1 1 calc R U . . .
C9 C 0.6518(4) 0.3787(3) 0.5438(6) 0.0535(11) Uani 1 1 d . . . . .
C10 C 0.6376(4) 0.4643(2) 0.5375(5) 0.0465(10) Uani 1 1 d . . . . .
C11 C 0.5407(4) 0.5000(3) 0.4560(6) 0.0555(11) Uani 1 1 d . . . . .
H11 H 0.482192 0.470311 0.401112 0.067 Uiso 1 1 calc R U . . .
C12 C 0.5301(5) 0.5798(3) 0.4556(6) 0.0629(12) Uani 1 1 d . . . . .
H12 H 0.464407 0.603298 0.401562 0.076 Uiso 1 1 calc R U . . .
C13 C 0.6179(5) 0.6241(3) 0.5360(6) 0.0656(13) Uani 1 1 d . . . . .
H13 H 0.611412 0.677504 0.535630 0.079 Uiso 1 1 calc R U . . .
C14 C 0.7143(5) 0.5893(3) 0.6159(6) 0.0647(13) Uani 1 1 d . . . . .
H14 H 0.773336 0.619120 0.669273 0.078 Uiso 1 1 calc R U . . .
C15 C 0.7240(4) 0.5098(3) 0.6177(6) 0.0583(11) Uani 1 1 d . . . . .
H15 H 0.789267 0.486685 0.673325 0.070 Uiso 1 1 calc R U . . .
C16 C 0.5485(4) 0.2290(2) 0.6626(6) 0.0502(10) Uani 1 1 d . . . . .
C17 C 0.5835(6) 0.1498(4) 0.8937(7) 0.101(2) Uani 1 1 d . . . . .
H17A H 0.594775 0.192763 0.967197 0.152 Uiso 1 1 calc R U . . .
H17B H 0.634973 0.107892 0.928736 0.152 Uiso 1 1 calc R U . . .
H17C H 0.498902 0.133893 0.895996 0.152 Uiso 1 1 calc R U . . .
Cl1 Cl 0.25283(16) 0.02552(8) 0.1000(2) 0.0855(4) Uani 1 1 d . . . . .
O1 O 0.7313(3) 0.34942(19) 0.6280(6) 0.0864(13) Uani 1 1 d . . . . .
O2 O 0.4680(3) 0.26138(17) 0.7362(4) 0.0651(9) Uani 1 1 d . . . . .
O3 O 0.6166(3) 0.1723(2) 0.7263(5) 0.0752(10) 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 0.0033 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 C6 121.9(4) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 Cl1 119.4(4) . . ?
C2 C3 Cl1 119.8(4) . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.2(4) . . ?
C1 C6 C7 120.4(4) . . ?
C5 C6 C7 122.2(4) . . ?
C16 C7 C6 107.0(3) . . ?
C16 C7 C8 109.7(3) . . ?
C6 C7 C8 113.9(3) . . ?
C16 C7 H7 108.7 . . ?
C6 C7 H7 108.7 . . ?
C8 C7 H7 108.7 . . ?
C9 C8 C7 111.7(4) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
O1 C9 C10 120.7(4) . . ?
O1 C9 C8 120.7(4) . . ?
C10 C9 C8 118.6(4) . . ?
C15 C10 C11 118.6(4) . . ?
C15 C10 C9 118.8(4) . . ?
C11 C10 C9 122.6(4) . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.0(5) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.8(4) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O2 C16 O3 124.2(4) . . ?
O2 C16 C7 124.0(4) . . ?
O3 C16 C7 111.7(4) . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 O3 C17 114.7(4) . . ?
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 1.380(6) . ?
C1 C6 1.383(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(6) . ?
C3 Cl1 1.738(4) . ?
C4 C5 1.385(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.523(6) . ?
C7 C16 1.519(6) . ?
C7 C8 1.523(6) . ?
C7 H7 0.9800 . ?
C8 C9 1.515(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O1 1.210(5) . ?
C9 C10 1.495(6) . ?
C10 C15 1.386(6) . ?
C10 C11 1.387(6) . ?
C11 C12 1.389(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O2 1.197(5) . ?
C16 O3 1.334(5) . ?
C17 O3 1.448(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4 O2 0.93 2.57 3.428(5) 154.0 4_554 yes
C8 H8A O1 0.97 2.61 3.390(6) 137.4 4_654 yes
C17 H17B Cl1 0.96 2.98 3.925(6) 166.9 3_556 yes
