#------------------------------------------------------------------------------
#$Date: 2020-06-12 02:26:12 +0300 (Fri, 12 Jun 2020) $
#$Revision: 253109 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038488.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_4038488
loop_
_publ_author_name
'Wang, Yu-Jiang'
'Li, Xiao-Xiao'
'Chen, Zili'
_publ_section_title
;
 Gold-Catalyzed Diastereoselective Formal Intermolecular [4 + 2 + 1]
 Cycloaddition of 1,3-Dien-8-yne with Diazo Ester.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00146
_journal_year                    2020
_chemical_formula_moiety         'C24 H26 N O4 S'
_chemical_formula_sum            'C24 H26 N O4 S'
_chemical_formula_weight         424.52
_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             2019-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.11
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6268(11)
_cell_length_b                   13.5454(14)
_cell_length_c                   12.6269(11)
_cell_measurement_reflns_used    9308
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.934
_cell_measurement_theta_min      2.220
_cell_volume                     2132.4(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      199.98
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29074
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_min         2.220
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1401 before and 0.0629 after correction. The Ratio of minimum to maximum transmission is 0.7668. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             900
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0532
_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)+(0.0614P)²+1.1454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3476
_reflns_number_total             5089
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00146_si_002.cif
_cod_data_source_block           mo_wyj2019052301_0ma_a
_cod_database_code               4038488
_shelx_shelxl_version_number     2018/1
_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.
;
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N005(H005), C00F(H00F)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00C(H00D,H00E), C00K(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00G(H00G), C00H(H00H), C00I(H00I), C00L(H00L),
 C00M(H00M), C00N(H00N), C00P(H00P), C00R(H00S), C00S(H00T), C00T(H00U)
2.d Idealised Me refined as rotating group:
 C00Q(H00O,H00Q,H00R), C00U(H00V,H00W,H00X)
;
_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
S01 S 0.10001(4) 0.61141(5) 0.29844(4) 0.04497(19) Uani 1 1 d . . . . .
O002 O 0.21560(12) 0.26198(12) 0.77082(11) 0.0417(4) Uani 1 1 d . . . . .
O003 O 0.11482(15) 0.60667(15) 0.18890(12) 0.0611(5) Uani 1 1 d . . . . .
O004 O 0.23624(17) 0.14252(14) 0.65532(16) 0.0653(5) Uani 1 1 d . . . . .
N005 N 0.16479(13) 0.51791(14) 0.35903(13) 0.0370(4) Uani 1 1 d . . . . .
H005 H 0.124755 0.459853 0.323877 0.044 Uiso 1 1 calc R . . . .
O006 O -0.00553(13) 0.60818(15) 0.32624(15) 0.0635(5) Uani 1 1 d . . . . .
C007 C 0.41837(15) 0.33069(16) 0.73739(14) 0.0303(4) Uani 1 1 d . . . . .
C008 C 0.25686(15) 0.38267(15) 0.60299(14) 0.0299(4) Uani 1 1 d . . . . .
H008 H 0.214835 0.409749 0.651973 0.036 Uiso 1 1 calc R . . . .
C009 C 0.33046(15) 0.29816(15) 0.64555(14) 0.0299(4) Uani 1 1 d . . . . .
C00A C 0.45707(16) 0.31506(17) 0.51017(15) 0.0357(5) Uani 1 1 d . . . . .
H00A H 0.532275 0.305691 0.528786 0.043 Uiso 1 1 calc R . . . .
C00B C 0.38252(17) 0.24723(16) 0.55717(15) 0.0351(5) Uani 1 1 d . . . . .
H00B H 0.422984 0.188545 0.587829 0.042 Uiso 1 1 calc R . . . .
H00C H 0.325476 0.224369 0.499432 0.042 Uiso 1 1 calc R . . . .
C00C C 0.27548(16) 0.49797(17) 0.34360(15) 0.0355(5) Uani 1 1 d . . . . .
H00D H 0.323481 0.553775 0.369002 0.043 Uiso 1 1 calc R . . . .
H00E H 0.279842 0.484628 0.267322 0.043 Uiso 1 1 calc R . . . .
C00D C 0.24350(15) 0.42373(16) 0.50624(15) 0.0302(4) Uani 1 1 d . . . . .
C00E C 0.25691(16) 0.22379(17) 0.68979(15) 0.0348(5) Uani 1 1 d . . . . .
C00F C 0.30309(15) 0.40629(16) 0.41255(14) 0.0314(4) Uani 1 1 d . . . . .
H00F H 0.270311 0.347768 0.371538 0.038 Uiso 1 1 calc R . . . .
C00G C 0.42132(16) 0.38708(17) 0.44397(15) 0.0345(5) Uani 1 1 d . . . . .
H00G H 0.471220 0.427779 0.415439 0.041 Uiso 1 1 calc R . . . .
C00H C 0.25799(17) 0.75128(17) 0.32137(16) 0.0391(5) Uani 1 1 d . . . . .
H00H H 0.282854 0.720488 0.262327 0.047 Uiso 1 1 calc R . . . .
C00I C 0.47936(16) 0.25968(18) 0.79886(15) 0.0378(5) Uani 1 1 d . . . . .
H00I H 0.465843 0.191593 0.784555 0.045 Uiso 1 1 calc R . . . .
C00J C 0.16556(16) 0.71711(18) 0.35648(15) 0.0378(5) Uani 1 1 d . . . . .
C00K C 0.15906(17) 0.50219(18) 0.47337(16) 0.0403(5) Uani 1 1 d . . . . .
H00J H 0.087055 0.478740 0.483396 0.048 Uiso 1 1 calc R . . . .
H00K H 0.175981 0.563626 0.515101 0.048 Uiso 1 1 calc R . . . .
C00L C 0.43982(18) 0.42913(18) 0.76027(17) 0.0411(5) Uani 1 1 d . . . . .
H00L H 0.398604 0.478539 0.719178 0.049 Uiso 1 1 calc R . . . .
C00M C 0.31315(18) 0.82976(18) 0.37247(18) 0.0428(5) Uani 1 1 d . . . . .
H00M H 0.375342 0.853412 0.347004 0.051 Uiso 1 1 calc R . . . .
C00N C 0.12897(19) 0.76338(19) 0.44153(17) 0.0457(6) Uani 1 1 d . . . . .
H00N H 0.064845 0.741555 0.464603 0.055 Uiso 1 1 calc R . . . .
C00O C 0.2803(2) 0.87560(18) 0.46067(18) 0.0456(6) Uani 1 1 d . . . . .
C00P C 0.56036(17) 0.2881(2) 0.88149(17) 0.0486(7) Uani 1 1 d . . . . .
H00P H 0.601785 0.239196 0.923197 0.058 Uiso 1 1 calc R . . . .
C00Q C 0.13713(19) 0.2033(2) 0.81355(19) 0.0490(6) Uani 1 1 d . . . . .
H00O H 0.082818 0.180090 0.754680 0.073 Uiso 1 1 calc GR . . . .
H00Q H 0.102679 0.243469 0.862971 0.073 Uiso 1 1 calc GR . . . .
H00R H 0.172480 0.146452 0.852075 0.073 Uiso 1 1 calc GR . . . .
C00R C 0.1859(2) 0.8411(2) 0.49251(17) 0.0507(6) Uani 1 1 d . . . . .
H00S H 0.160285 0.872225 0.550972 0.061 Uiso 1 1 calc R . . . .
C00S C 0.58077(19) 0.3868(2) 0.90309(18) 0.0539(7) Uani 1 1 d . . . . .
H00T H 0.635939 0.405901 0.959483 0.065 Uiso 1 1 calc R . . . .
C00T C 0.5208(2) 0.4568(2) 0.84254(19) 0.0540(7) Uani 1 1 d . . . . .
H00U H 0.534721 0.524829 0.856900 0.065 Uiso 1 1 calc R . . . .
C00U C 0.3452(3) 0.9564(2) 0.5197(2) 0.0690(8) Uani 1 1 d . . . . .
H00V H 0.411769 0.928840 0.559096 0.104 Uiso 1 1 calc GR . . . .
H00W H 0.304008 0.987369 0.570319 0.104 Uiso 1 1 calc GR . . . .
H00X H 0.362430 1.005889 0.468475 0.104 Uiso 1 1 calc GR . . . .
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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 '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
O003 S01 N005 106.68(10) . . ?
O003 S01 O006 120.43(11) . . ?
O003 S01 C00J 108.43(11) . . ?
N005 S01 C00J 105.62(9) . . ?
O006 S01 N005 106.17(10) . . ?
O006 S01 C00J 108.56(11) . . ?
C00E O002 C00Q 116.89(18) . . ?
S01 N005 H005 102.8 . . ?
C00C N005 S01 119.90(14) . . ?
C00C N005 H005 102.8 . . ?
C00C N005 C00K 107.42(14) . . ?
C00K N005 S01 118.26(15) . . ?
C00K N005 H005 102.8 . . ?
C00I C007 C009 119.54(19) . . ?
C00L C007 C009 121.90(18) . . ?
C00L C007 C00I 118.56(18) . . ?
C009 C008 H008 115.7 . . ?
C00D C008 H008 115.7 . . ?
C00D C008 C009 128.51(18) . . ?
C007 C009 C00B 109.51(16) . . ?
C008 C009 C007 112.29(17) . . ?
C008 C009 C00B 112.82(15) . . ?
C008 C009 C00E 104.60(16) . . ?
C00E C009 C007 108.66(15) . . ?
C00E C009 C00B 108.74(17) . . ?
C00B C00A H00A 119.0 . . ?
C00G C00A H00A 119.0 . . ?
C00G C00A C00B 122.02(19) . . ?
C009 C00B H00B 109.2 . . ?
C009 C00B H00C 109.2 . . ?
C00A C00B C009 112.15(17) . . ?
C00A C00B H00B 109.2 . . ?
C00A C00B H00C 109.2 . . ?
H00B C00B H00C 107.9 . . ?
N005 C00C H00D 111.3 . . ?
N005 C00C H00E 111.3 . . ?
N005 C00C C00F 102.16(16) . . ?
H00D C00C H00E 109.2 . . ?
C00F C00C H00D 111.3 . . ?
C00F C00C H00E 111.3 . . ?
C008 C00D C00F 130.18(18) . . ?
C008 C00D C00K 121.78(18) . . ?
C00K C00D C00F 108.04(16) . . ?
O002 C00E C009 111.09(18) . . ?
O004 C00E O002 123.4(2) . . ?
O004 C00E C009 125.53(19) . . ?
C00C C00F H00F 108.1 . . ?
C00D C00F C00C 102.80(16) . . ?
C00D C00F H00F 108.1 . . ?
C00G C00F C00C 114.76(17) . . ?
C00G C00F C00D 114.51(15) . . ?
C00G C00F H00F 108.1 . . ?
C00A C00G C00F 121.41(19) . . ?
C00A C00G H00G 119.3 . . ?
C00F C00G H00G 119.3 . . ?
C00J C00H H00H 120.1 . . ?
C00M C00H H00H 120.1 . . ?
C00M C00H C00J 119.7(2) . . ?
C007 C00I H00I 119.9 . . ?
C007 C00I C00P 120.2(2) . . ?
C00P C00I H00I 119.9 . . ?
C00H C00J S01 120.14(17) . . ?
C00N C00J S01 120.01(18) . . ?
C00N C00J C00H 119.7(2) . . ?
N005 C00K C00D 103.19(16) . . ?
N005 C00K H00J 111.1 . . ?
N005 C00K H00K 111.1 . . ?
C00D C00K H00J 111.1 . . ?
C00D C00K H00K 111.1 . . ?
H00J C00K H00K 109.1 . . ?
C007 C00L H00L 119.6 . . ?
C007 C00L C00T 120.9(2) . . ?
C00T C00L H00L 119.6 . . ?
C00H C00M H00M 119.1 . . ?
C00H C00M C00O 121.8(2) . . ?
C00O C00M H00M 119.1 . . ?
C00J C00N H00N 120.1 . . ?
C00R C00N C00J 119.7(2) . . ?
C00R C00N H00N 120.1 . . ?
C00M C00O C00R 117.1(2) . . ?
C00M C00O C00U 121.0(2) . . ?
C00R C00O C00U 121.8(2) . . ?
C00I C00P H00P 119.8 . . ?
C00S C00P C00I 120.5(2) . . ?
C00S C00P H00P 119.8 . . ?
O002 C00Q H00O 109.5 . . ?
O002 C00Q H00Q 109.5 . . ?
O002 C00Q H00R 109.5 . . ?
H00O C00Q H00Q 109.5 . . ?
H00O C00Q H00R 109.5 . . ?
H00Q C00Q H00R 109.5 . . ?
C00N C00R C00O 121.8(2) . . ?
C00N C00R H00S 119.1 . . ?
C00O C00R H00S 119.1 . . ?
C00P C00S H00T 120.3 . . ?
C00T C00S C00P 119.4(2) . . ?
C00T C00S H00T 120.3 . . ?
C00L C00T H00U 119.8 . . ?
C00S C00T C00L 120.5(3) . . ?
C00S C00T H00U 119.8 . . ?
C00O C00U H00V 109.5 . . ?
C00O C00U H00W 109.5 . . ?
C00O C00U H00X 109.5 . . ?
H00V C00U H00W 109.5 . . ?
H00V C00U H00X 109.5 . . ?
H00W C00U H00X 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
S01 O003 1.4261(18) . ?
S01 N005 1.6310(18) . ?
S01 O006 1.4315(18) . ?
S01 C00J 1.755(3) . ?
O002 C00E 1.325(2) . ?
O002 C00Q 1.440(2) . ?
O004 C00E 1.197(3) . ?
N005 H005 1.0000 . ?
N005 C00C 1.466(3) . ?
N005 C00K 1.472(2) . ?
C007 C009 1.538(3) . ?
C007 C00I 1.390(3) . ?
C007 C00L 1.382(3) . ?
C008 H008 0.9500 . ?
C008 C009 1.518(3) . ?
C008 C00D 1.329(3) . ?
C009 C00B 1.544(3) . ?
C009 C00E 1.534(3) . ?
C00A H00A 0.9500 . ?
C00A C00B 1.503(3) . ?
C00A C00G 1.317(3) . ?
C00B H00B 0.9900 . ?
C00B H00C 0.9900 . ?
C00C H00D 0.9900 . ?
C00C H00E 0.9900 . ?
C00C C00F 1.525(3) . ?
C00D C00F 1.518(3) . ?
C00D C00K 1.516(3) . ?
C00F H00F 1.0000 . ?
C00F C00G 1.505(3) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00H C00J 1.392(3) . ?
C00H C00M 1.375(3) . ?
C00I H00I 0.9500 . ?
C00I C00P 1.395(3) . ?
C00J C00N 1.385(3) . ?
C00K H00J 0.9900 . ?
C00K H00K 0.9900 . ?
C00L H00L 0.9500 . ?
C00L C00T 1.389(3) . ?
C00M H00M 0.9500 . ?
C00M C00O 1.394(3) . ?
C00N H00N 0.9500 . ?
C00N C00R 1.376(4) . ?
C00O C00R 1.397(4) . ?
C00O C00U 1.494(4) . ?
C00P H00P 0.9500 . ?
C00P C00S 1.380(4) . ?
C00Q H00O 0.9800 . ?
C00Q H00Q 0.9800 . ?
C00Q H00R 0.9800 . ?
C00R H00S 0.9500 . ?
C00S H00T 0.9500 . ?
C00S C00T 1.369(4) . ?
C00T H00U 0.9500 . ?
C00U H00V 0.9800 . ?
C00U H00W 0.9800 . ?
C00U H00X 0.9800 . ?
