Alkenylation of unactivated alkyl bromides through visible light photocatalysis
Xiao, Wen-Jing; Zhou, Quan-Quan; Düsel, Simon Josef; Lu, Liang-Qiu; König, Burkhard; Chemical Communications  (2018) –; doi:10.1039/C8CC08362B

data_7122639
_publ_section_title
;
 Alkenylation of unactivated alkyl bromides through visible light
 photocatalysis
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08362B
_journal_year                    2018
_chemical_formula_moiety         '0.5(C33 H40 O)'
_chemical_formula_sum            'C16.5 H20 O0.5'
_chemical_formula_weight         226.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc21352f
_audit_creation_date             2018-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-11-19 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.658(2)
_cell_length_b                   11.271(3)
_cell_length_c                   27.041(6)
_cell_measurement_reflns_used    2381
_cell_measurement_temperature    297.15(10)
_cell_measurement_theta_max      24.812
_cell_measurement_theta_min      2.469
_cell_volume                     2638.8(11)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'SMART (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.15(10)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21025
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.534
_diffrn_reflns_theta_min         1.958
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6230
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1465 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.8358.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.116
_refine_diff_density_min         -0.105
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   4(3)
_refine_ls_extinction_coef       0.0065(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0457
_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/[\s^2^(Fo^2^)+(0.0465P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1140
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3079
_reflns_number_total             5463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08362b2.cif
_cod_data_source_block           mo_180515e_0m
_cod_original_formula_sum        'C16.50 H20 O0.50'
_cod_database_code               7122639
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: -3(3)
 4(3)
2. 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
3.a Ternary CH refined with riding coordinates:
 C15(H15), C17(H17), C20(H20), C21(H21), C28(H28)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B), C22(H22A,H22B), C23(H23A,
 H23B), C26(H26A,H26B), C27(H27A,H27B), C30(H30A,H30B), C31(H31A,H31B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              46305
_olex2_submission_special_instructions 'No special instructions were received'