Solvent-controlled photocatalytic divergent cyclization of alkynyl aldehydes: access to cyclopentenones and dihydropyranols
Zhu, Haiqian; Zheng, Hanliang; Zhang, Junhua; Feng, Jian; Kong, Lichun; Zhang, Fang; Xue, Xiao-Song; Zhu, Gangguo; Chemical Science  (2021) –; doi:10.1039/D1SC03416B

data_1564313
_publ_section_title
;
 Solvent-controlled photocatalytic divergent cyclization of alkynyl
 aldehydes: access to cyclopentenones and dihydropyranols
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC03416B
_journal_year                    2021
_chemical_formula_moiety         'C21 H19 N O3 S'
_chemical_formula_sum            'C21 H19 N O3 S'
_chemical_formula_weight         365.44
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2021-01-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2021-02-03 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.831(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8167(2)
_cell_length_b                   17.2043(6)
_cell_length_c                   19.0214(8)
_cell_measurement_reflns_used    9554
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.43
_cell_volume                     1902.54(12)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      250.0
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19469
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.368
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6907
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0756 before and 0.0429 after correction.
The Ratio of minimum to maximum transmission is 0.9264.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0456
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0899P)^2^+0.3573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1580
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3717
_reflns_number_total             4289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc03416b2.cif
_cod_data_source_block           a_a
_cod_depositor_comments
;

2022-06-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C5.25 H4.75 N0.25 O0.75 S0.25'
_cod_original_formula_weight         91.36
_cod_original_formula_moiety         '0.25(C21 H19 N O3 S)'
_cod_original_formula_units_Z            16
_cod_database_code               1564313
_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:
 C008(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L),
 C00O(H00O), C00Q(H00S)
2.c Idealised Me refined as rotating group:
 C00M(H00C,H00E,H00G), C00N(H00M,H00N,H00I), C00P(H00P,H00Q,H00R)
;
_shelx_shelxl_version_number     2017/1
_olex2_submission_special_instructions 'No special instructions were received'