Rhodium(iii) catalyzed olefination and deuteration of tetrahydrocarbazole
Peng, Wan; Liu, Qiaohong; Yin, Fucheng; Shi, Cunjian; Ji, Limei; Qu, Lailiang; Wang, Cheng; Luo, Heng; Kong, Lingyi; Wang, Xiaobing; RSC Advances 11 (2021) 8356–8361; doi:10.1039/D1RA00236H

data_7242305
_publ_section_title
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 Rhodium(iii) catalyzed olefination and deuteration of tetrahydrocarbazole
;
_journal_issue                   14
_journal_name_full               'RSC Advances'
_journal_page_first              8356
_journal_page_last               8361
_journal_paper_doi               10.1039/D1RA00236H
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C21 H25 F N2 O3'
_chemical_formula_sum            'C21 H25 F N2 O3'
_chemical_formula_weight         372.43
_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     dual
_audit_creation_date             2020-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-28 deposited with the CCDC.	2021-01-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.0440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4277(3)
_cell_length_b                   8.5846(2)
_cell_length_c                   22.3869(5)
_cell_measurement_reflns_used    9385
_cell_measurement_temperature    170
_cell_measurement_theta_max      72.428
_cell_measurement_theta_min      5.524
_cell_volume                     1984.30(9)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17958
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        63.675
_diffrn_reflns_theta_max         63.675
_diffrn_reflns_theta_min         5.526
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1329 before and 0.0654 after correction. The Ratio of minimum to maximum transmission is 0.8585. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3203
_refine_ls_number_restraints     298
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0689P)^2^+0.5773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2738
_reflns_number_total             3203
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra00236h2.cif
_cod_data_source_block           cu_22020375_0m
_cod_database_code               7242305
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 O3-C19 \\sim O4-C19
 with sigma of 0.02
 O3-C22 \\sim O4-C23
 with sigma of 0.02
 C25-C22 \\sim C23-C24
 with sigma of 0.02
3. Rigid bond restraints
 C24, C23, C22, C25, O3, O4, O2, C19
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Others
 Fixed Sof: H9AA(0.75) H9AB(0.75) H9BC(0.25) H9BD(0.25) H14A(0.75) H14B(0.75)
 H14C(0.25) H14D(0.25) H15A(0.75) H15B(0.75) H15C(0.75) H15D(0.25) H15E(0.25)
 H15F(0.25) O3(0.5) C12(0.75) H12A(0.75) H12B(0.75) C11(0.75) H11(0.75) O4(0.5)
 C13(0.25) H13A(0.25) H13B(0.25) C10(0.25) H10(0.25) C22(0.5) H22A(0.5)
 H22B(0.5) C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5) C24(0.5) H24A(0.5) H24B(0.5)
 H24C(0.5) C23(0.5) H23A(0.5) H23B(0.5)
6.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9AA,H9AB), C9(H9BC,H9BD), C14(H14A,H14B), C14(H14C,H14D), C12(H12A,H12B),
 C13(H13A,H13B), C22(H22A,H22B), C23(H23A,H23B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C21(H21), C6(H6), C20(H20)
6.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C15(H15D,H15E,H15F), C17(H17A,H17B,
 H17C), C25(H25A,H25B,H25C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'