Lithium Dicyclohexylamide in Transition-Metal-Free Fischer-Tropsch Chemistry.
Xu, Maotong; Qu, Zheng-Wang; Grimme, Stefan; Stephan, Douglas W.; Journal of the American Chemical Society 143 (2021) 634–638; doi:10.1021/jacs.0c11482

data_4135569
_publ_section_title
;
 Lithium Dicyclohexylamide in Transition-Metal-Free Fischer-Tropsch
 Chemistry.
;
_journal_issue                   2
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              634
_journal_page_last               638
_journal_paper_doi               10.1021/jacs.0c11482
_journal_volume                  143
_journal_year                    2021
_chemical_formula_moiety         'C28 H47 N2 O4.5, 1.5(C4 H8 O), 0.5(H2 O)'
_chemical_formula_sum            'C34 H60 N2 O6.5'
_chemical_formula_weight         600.84
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-12-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.4096(16)
_cell_length_b                   19.4096(16)
_cell_length_c                   19.5602(19)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.90
_cell_measurement_theta_min      2.56
_cell_volume                     7369.0(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      149.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.2021
_diffrn_reflns_av_unetI/netI     0.1160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            116649
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.183
_diffrn_reflns_theta_min         2.557
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6495
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0866 before and 0.0749 after correction.
The Ratio of minimum to maximum transmission is 0.8712.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       SHARD
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1577 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         8179
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1764
_refine_ls_R_factor_gt           0.0839
_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^)+(0.1409P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1921
_refine_ls_wR_factor_ref         0.2396
_reflns_Friedel_coverage         0.939
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4337
_reflns_number_total             8179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Cy2NC(O)(COH)2C(O)NCy2.cif
_cod_data_source_block           final_a
_cod_original_cell_volume        7369.0(14)
_cod_original_formula_sum        'C34 H60 N2 O6.50'
_cod_database_code               4135569
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.996
_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 O(H) groups, All O(H,H) groups
2. Rigid bond restraints
 C36, C35, C34, C33
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C36 \\sim C35 \\sim C34 \\sim C33: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
4. Others
 Fixed Sof: C36(0.5) H36B(0.5) H36A(0.5) C35(0.5) H35A(0.5) H35B(0.5) C34(0.5)
 H34A(0.5) H34B(0.5) C33(0.5) H33B(0.5) H33A(0.5) O9(0.5) H9C(0.5) H9D(0.5)
 O8(0.5) H8C(0.5) H8D(0.5) O10(0.5)
5.a Free rotating group:
 O9(H9C,H9D), O8(H8C,H8D)
5.b Ternary CH refined with riding coordinates:
 C7(H7), C1(H1), C23(H23), C17(H17)
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C6(H6A,H6B), C2(H2A,H2B), C22(H22A,H22B), C9(H9A,H9B), C12(H12A,
 H12B), C5(H5A,H5B), C11(H11A,H11B), C28(H28A,H28B), C10(H10A,H10B), C32(H32A,
 H32B), C27(H27A,H27B), C21(H21A,H21B), C20(H20A,H20B), C3(H3A,H3B), C29(H29A,
 H29B), C18(H18A,H18B), C00X(H00A,H00B), C24(H24A,H24B), C31(H31A,H31B), C4(H4A,
 H4B), C25(H25A,H25B), C26(H26A,H26B), C30(H30A,H30B), C36(H36B,H36A), C35(H35A,
 H35B), C34(H34A,H34B), C33(H33B,H33A)
5.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2)
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_shelx_res_checksum              80473
_shelx_hkl_checksum              4702
_olex2_submission_special_instructions 'No special instructions were received'