#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:25:26 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290799 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/28/7132855.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_7132855
loop_
_publ_author_name
'Gopalakrishnan, Dinesh Kumar'
'Bhardwaj, Srashti'
'Kumar, Sandeep'
'Karmakar, Tarak'
'Vaitla, Janakiram'
_publ_section_title
;
 Carbene-mediated stereoselective olefination of vinyl sulfoxonium ylides
 with diazo compounds and acetals.
;
_journal_issue                   28
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3846
_journal_page_last               3849
_journal_paper_doi               10.1039/d4cc00450g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C21 H18 O4'
_chemical_formula_sum            'C21 H18 O4'
_chemical_formula_weight         334.35
_chemical_name_systematic        Dienoate
_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_block_doi                 10.5517/ccdc.csd.cc2hnqkg
_audit_creation_date             2023-12-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-12 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                91.975(4)
_cell_angle_beta                 93.296(4)
_cell_angle_gamma                108.179(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4870(10)
_cell_length_b                   10.1115(12)
_cell_length_c                   10.5324(11)
_cell_measurement_reflns_used    9902
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      30.73
_cell_measurement_theta_min      2.53
_cell_volume                     856.01(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_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  0.0448
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42554
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.304
_diffrn_reflns_theta_min         2.123
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6962
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0782 before and 0.0568 after correction.
The Ratio of minimum to maximum transmission is 0.9327.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'dull whiteish white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_preparation       'As mentioned in the paper'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         6039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0508
_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)+(0.0858P)²+0.1571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1675
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4272
_reflns_number_total             6039
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00450g2.cif
_cod_data_source_block           121223_6mem_1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7132854--7132855.cif.'
_cod_database_code               7132855
_shelx_shelxl_version_number     2019/1
_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 Secondary CH2 refined with riding coordinates:
 C00E(H00B,H00C), C00O(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N)
2.c Idealised Me refined as rotating group:
 C00P(H00O,H00P,H00Q)
;
_olex2_submission_original_sample_id Dienoate
_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
O001 O 0.43639(12) 0.84780(10) 0.03551(9) 0.0477(2) Uani 1 1 d . . . . .
O002 O 0.16715(12) 0.75059(12) 0.03913(10) 0.0552(3) Uani 1 1 d . . . . .
O003 O 0.55061(13) 0.76517(10) 0.60988(9) 0.0552(3) Uani 1 1 d . . . . .
O004 O 0.51755(17) 0.82408(11) 0.41111(10) 0.0720(4) Uani 1 1 d . . . . .
C005 C 0.33917(13) 0.66165(11) 0.17770(10) 0.0347(2) Uani 1 1 d . . . . .
C006 C 0.49382(13) 0.62703(11) 0.16529(10) 0.0349(2) Uani 1 1 d . . . . .
C007 C 0.62655(14) 0.73111(13) 0.12105(11) 0.0407(2) Uani 1 1 d . . . . .
C008 C 0.23149(14) 0.62393(12) 0.26739(11) 0.0376(2) Uani 1 1 d . . . . .
H008 H 0.136132 0.650459 0.257956 0.045 Uiso 1 1 calc R U . . .
C009 C 0.30366(15) 0.75452(12) 0.08009(11) 0.0395(2) Uani 1 1 d . . . . .
C00A C 0.36103(16) 0.59796(13) 0.47795(11) 0.0424(3) Uani 1 1 d . . . . .
H00A H 0.364190 0.539980 0.544045 0.051 Uiso 1 1 calc R U . . .
C00B C 0.24722(14) 0.54417(12) 0.38069(10) 0.0364(2) Uani 1 1 d . . . . .
C00C C 0.11961(14) 0.40528(12) 0.38487(11) 0.0383(2) Uani 1 1 d . . . . .
C00D C 0.50940(15) 0.49668(13) 0.18704(11) 0.0410(2) Uani 1 1 d . . . . .
H00D H 0.421144 0.426802 0.216092 0.049 Uiso 1 1 calc R U . . .
C00E C 0.59806(16) 0.86783(13) 0.10209(13) 0.0484(3) Uani 1 1 d . . . . .
H00B H 0.603712 0.916206 0.184201 0.058 Uiso 1 1 calc R U . . .
H00C H 0.684714 0.925165 0.053146 0.058 Uiso 1 1 calc R U . . .
C00F C 0.48173(17) 0.73969(13) 0.49085(12) 0.0450(3) Uani 1 1 d . . . . .
C00G C 0.77343(16) 0.70446(16) 0.09856(13) 0.0515(3) Uani 1 1 d . . . . .
H00G H 0.861895 0.773712 0.068998 0.062 Uiso 1 1 calc R U . . .
C00H C 0.65775(18) 0.47142(16) 0.16509(13) 0.0493(3) Uani 1 1 d . . . . .
H00H H 0.669207 0.384793 0.180677 0.059 Uiso 1 1 calc R U . . .
C00I C 0.02587(18) 0.34031(14) 0.27456(13) 0.0504(3) Uani 1 1 d . . . . .
H00I H 0.045325 0.383734 0.197990 0.060 Uiso 1 1 calc R U . . .
C00J C 0.78790(17) 0.57425(18) 0.12030(14) 0.0545(3) Uani 1 1 d . . . . .
H00J H 0.886089 0.556079 0.104583 0.065 Uiso 1 1 calc R U . . .
C00K C 0.08760(19) 0.33688(15) 0.49834(13) 0.0528(3) Uani 1 1 d . . . . .
H00K H 0.147974 0.378222 0.573756 0.063 Uiso 1 1 calc R U . . .
C00L C -0.0960(2) 0.21210(16) 0.27639(17) 0.0630(4) Uani 1 1 d . . . . .
H00L H -0.157903 0.170555 0.201587 0.076 Uiso 1 1 calc R U . . .
C00M C -0.0330(2) 0.20845(16) 0.49915(15) 0.0634(4) Uani 1 1 d . . . . .
H00M H -0.051838 0.163529 0.575030 0.076 Uiso 1 1 calc R U . . .
C00N C -0.1257(2) 0.14597(17) 0.38906(17) 0.0630(4) Uani 1 1 d . . . . .
H00N H -0.207646 0.059973 0.390683 0.076 Uiso 1 1 calc R U . . .
C00O C 0.6726(2) 0.90138(16) 0.63806(15) 0.0609(4) Uani 1 1 d . . . . .
H00E H 0.626826 0.973883 0.612279 0.073 Uiso 1 1 calc R U . . .
H00F H 0.770889 0.909545 0.592368 0.073 Uiso 1 1 calc R U . . .
C00P C 0.7158(3) 0.9159(2) 0.77694(18) 0.0769(5) Uani 1 1 d . . . . .
H00O H 0.797923 1.004841 0.798342 0.115 Uiso 1 1 calc R U . . .
H00P H 0.759506 0.842999 0.801537 0.115 Uiso 1 1 calc R U . . .
H00Q H 0.618053 0.909453 0.821127 0.115 Uiso 1 1 calc R U . . .
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
C009 O001 C00E 117.51(9) . . ?
C00F O003 C00O 116.09(11) . . ?
C006 C005 C009 115.29(9) . . ?
C008 C005 C006 127.74(10) . . ?
C008 C005 C009 116.93(10) . . ?
C007 C006 C005 116.17(10) . . ?
C00D C006 C005 123.85(10) . . ?
C00D C006 C007 119.85(11) . . ?
C006 C007 C00E 115.73(11) . . ?
C00G C007 C006 120.06(12) . . ?
C00G C007 C00E 124.21(11) . . ?
C005 C008 H008 116.4 . . ?
C005 C008 C00B 127.12(10) . . ?
C00B C008 H008 116.4 . . ?
O001 C009 C005 116.42(10) . . ?
O002 C009 O001 118.69(10) . . ?
O002 C009 C005 124.89(11) . . ?
C00B C00A H00A 116.7 . . ?
C00B C00A C00F 126.67(10) . . ?
C00F C00A H00A 116.7 . . ?
C00A C00B C008 122.31(10) . . ?
C00A C00B C00C 121.73(10) . . ?
C00C C00B C008 115.76(10) . . ?
C00I C00C C00B 120.16(10) . . ?
C00I C00C C00K 117.90(11) . . ?
C00K C00C C00B 121.93(11) . . ?
C006 C00D H00D 120.2 . . ?
C006 C00D C00H 119.60(12) . . ?
C00H C00D H00D 120.2 . . ?
O001 C00E C007 110.86(10) . . ?
O001 C00E H00B 109.5 . . ?
O001 C00E H00C 109.5 . . ?
C007 C00E H00B 109.5 . . ?
C007 C00E H00C 109.5 . . ?
H00B C00E H00C 108.1 . . ?
O003 C00F C00A 109.38(10) . . ?
O004 C00F O003 122.40(12) . . ?
O004 C00F C00A 128.22(12) . . ?
C007 C00G H00G 120.1 . . ?
C00J C00G C007 119.74(13) . . ?
C00J C00G H00G 120.1 . . ?
C00D C00H H00H 119.9 . . ?
C00J C00H C00D 120.28(13) . . ?
C00J C00H H00H 119.9 . . ?
C00C C00I H00I 119.4 . . ?
C00L C00I C00C 121.28(12) . . ?
C00L C00I H00I 119.4 . . ?
C00G C00J H00J 119.8 . . ?
C00H C00J C00G 120.46(12) . . ?
C00H C00J H00J 119.8 . . ?
C00C C00K H00K 119.8 . . ?
C00M C00K C00C 120.47(13) . . ?
C00M C00K H00K 119.8 . . ?
C00I C00L H00L 120.0 . . ?
C00I C00L C00N 120.06(14) . . ?
C00N C00L H00L 120.0 . . ?
C00K C00M H00M 119.6 . . ?
C00N C00M C00K 120.87(13) . . ?
C00N C00M H00M 119.6 . . ?
C00L C00N H00N 120.3 . . ?
C00M C00N C00L 119.41(13) . . ?
C00M C00N H00N 120.3 . . ?
O003 C00O H00E 110.2 . . ?
O003 C00O H00F 110.2 . . ?
O003 C00O C00P 107.57(13) . . ?
H00E C00O H00F 108.5 . . ?
C00P C00O H00E 110.2 . . ?
C00P C00O H00F 110.2 . . ?
C00O C00P H00O 109.5 . . ?
C00O C00P H00P 109.5 . . ?
C00O C00P H00Q 109.5 . . ?
H00O C00P H00P 109.5 . . ?
H00O C00P H00Q 109.5 . . ?
H00P C00P H00Q 109.5 . . ?
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
O001 C009 1.3444(14) . ?
O001 C00E 1.4566(16) . ?
O002 C009 1.2010(15) . ?
O003 C00F 1.3339(16) . ?
O003 C00O 1.4503(17) . ?
O004 C00F 1.2011(15) . ?
C005 C006 1.4716(15) . ?
C005 C008 1.3340(15) . ?
C005 C009 1.4957(15) . ?
C006 C007 1.3958(15) . ?
C006 C00D 1.3904(16) . ?
C007 C00E 1.4938(19) . ?
C007 C00G 1.3863(18) . ?
C008 H008 0.9300 . ?
C008 C00B 1.4858(15) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.3410(17) . ?
C00A C00F 1.4752(17) . ?
C00B C00C 1.4859(16) . ?
C00C C00I 1.3890(18) . ?
C00C C00K 1.3991(17) . ?
C00D H00D 0.9300 . ?
C00D C00H 1.3906(18) . ?
C00E H00B 0.9700 . ?
C00E H00C 0.9700 . ?
C00G H00G 0.9300 . ?
C00G C00J 1.385(2) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.379(2) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.3851(19) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00M 1.3808(19) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.379(2) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.377(2) . ?
C00N H00N 0.9300 . ?
C00O H00E 0.9700 . ?
C00O H00F 0.9700 . ?
C00O C00P 1.478(2) . ?
C00P H00O 0.9600 . ?
C00P H00P 0.9600 . ?
C00P H00Q 0.9600 . ?
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
C005 C006 C007 C00E 4.70(15) . . . . ?
C005 C006 C007 C00G -175.80(11) . . . . ?
C005 C006 C00D C00H 175.96(11) . . . . ?
C005 C008 C00B C00A 68.97(18) . . . . ?
C005 C008 C00B C00C -116.05(13) . . . . ?
C006 C005 C008 C00B 3.7(2) . . . . ?
C006 C005 C009 O001 -31.56(15) . . . . ?
C006 C005 C009 O002 147.89(13) . . . . ?
C006 C007 C00E O001 -45.78(14) . . . . ?
C006 C007 C00G C00J -0.07(19) . . . . ?
C006 C00D C00H C00J -0.92(19) . . . . ?
C007 C006 C00D C00H 0.34(17) . . . . ?
C007 C00G C00J C00H -0.5(2) . . . . ?
C008 C005 C006 C007 -143.36(12) . . . . ?
C008 C005 C006 C00D 40.87(18) . . . . ?
C008 C005 C009 O001 146.28(11) . . . . ?
C008 C005 C009 O002 -34.27(18) . . . . ?
C008 C00B C00C C00I 18.03(17) . . . . ?
C008 C00B C00C C00K -160.90(12) . . . . ?
C009 O001 C00E C007 49.72(15) . . . . ?
C009 C005 C006 C007 34.21(14) . . . . ?
C009 C005 C006 C00D -141.56(11) . . . . ?
C009 C005 C008 C00B -173.81(11) . . . . ?
C00A C00B C00C C00I -166.96(13) . . . . ?
C00A C00B C00C C00K 14.10(19) . . . . ?
C00B C00A C00F O003 167.44(13) . . . . ?
C00B C00A C00F O004 -12.2(3) . . . . ?
C00B C00C C00I C00L -178.74(14) . . . . ?
C00B C00C C00K C00M 179.37(14) . . . . ?
C00C C00I C00L C00N -0.4(3) . . . . ?
C00C C00K C00M C00N -0.9(3) . . . . ?
C00D C006 C007 C00E -179.34(11) . . . . ?
C00D C006 C007 C00G 0.15(17) . . . . ?
C00D C00H C00J C00G 1.0(2) . . . . ?
C00E O001 C009 O002 169.27(12) . . . . ?
C00E O001 C009 C005 -11.24(16) . . . . ?
C00E C007 C00G C00J 179.38(12) . . . . ?
C00F O003 C00O C00P 172.28(15) . . . . ?
C00F C00A C00B C008 1.6(2) . . . . ?
C00F C00A C00B C00C -173.03(12) . . . . ?
C00G C007 C00E O001 134.75(13) . . . . ?
C00I C00C C00K C00M 0.4(2) . . . . ?
C00I C00L C00N C00M -0.1(3) . . . . ?
C00K C00C C00I C00L 0.2(2) . . . . ?
C00K C00M C00N C00L 0.8(3) . . . . ?
C00O O003 C00F O004 -0.2(2) . . . . ?
C00O O003 C00F C00A -179.85(13) . . . . ?
