#------------------------------------------------------------------------------
#$Date: 2021-02-04 02:37:01 +0200 (Thu, 04 Feb 2021) $
#$Revision: 261450 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/55/4135571.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_4135571
loop_
_publ_author_name
'Xu, Maotong'
'Qu, Zheng-Wang'
'Grimme, Stefan'
'Stephan, Douglas W.'
_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         'C26 H46 N2 O2'
_chemical_formula_sum            'C26 H46 N2 O2'
_chemical_formula_weight         418.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2019-10-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                112.478(5)
_cell_angle_beta                 91.182(6)
_cell_angle_gamma                115.343(5)
_cell_formula_units_Z            2
_cell_length_a                   10.3158(11)
_cell_length_b                   10.9502(11)
_cell_length_c                   13.2446(15)
_cell_measurement_reflns_used    7014
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.32
_cell_volume                     1218.6(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.9955
_diffrn_measured_fraction_theta_max 0.9955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18508
_diffrn_reflns_theta_full        27.1028
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         3.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7103
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0507 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.9527.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.1409
_exptl_crystal_description       shard
_exptl_crystal_F_000             464.1828
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.6835
_refine_diff_density_min         -0.7054
_refine_diff_density_rms         0.0534
_refine_ls_d_res_high            0.7800
_refine_ls_d_res_low             6.4404
_refine_ls_goodness_of_fit_ref   1.0313
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    72
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5355
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0313
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0574P)²+0.4643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              12
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                4142
_reflns_number_total             5355
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            1-f_a.cif
_cod_data_source_block           f_a
_cod_database_code               4135571
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C0AA(H0AA), C44(H44), C38(H38), C4(H4), C51(H51)
2.b Secondary CH2 refined with riding coordinates:
 C39(H39a,H39b), C46(H46a,H46b), C13(H13a,H13b), C43(H43a,H43b), C45(H45a,
 H45b), C16(H16a,H16b), C17(H17a,H17b), C1(H1a,H1b), C5(H5a,H5b), C3(H3a,H3b),
 C49(H49a,H49b), C48(H48a,H48b), C2(H2a,H2b), C6(H6a,H6b), C40(H40a,H40b),
 C41(H41a,H41b), C42(H42a,H42b), C47(H47a,H47b), C30(H30a,H30b), C50(H50a,H50b)
2.c Tetrahedral OH refined with riding coordinates:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
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_refinement_flags_posn
N1 N 0.31988(12) 0.87293(12) 0.20583(10) 0.0195(3) Uani 1.000000 .
N2 N 0.08454(12) 0.61436(12) 0.24546(9) 0.0180(2) Uani 1.000000 .
C0AA C 0.05338(15) 0.70370(14) 0.34794(11) 0.0201(3) Uani 1.000000 .
H0AA H 0.08207(15) 0.80100(14) 0.34726(11) 0.0241(3) Uiso 1.000000 R
C44 C 0.03067(15) 0.45432(14) 0.21849(12) 0.0204(3) Uani 1.000000 .
H44 H 0.02127(15) 0.44567(14) 0.28925(12) 0.0245(3) Uiso 1.000000 R
C38 C 0.39414(14) 0.77863(14) 0.17334(12) 0.0209(3) Uani 1.000000 .
H38 H 0.31719(14) 0.67390(14) 0.13636(12) 0.0251(4) Uiso 1.000000 R
C4 C 0.41510(15) 1.03794(14) 0.25987(12) 0.0215(3) Uani 1.000000 .
H4 H 0.51670(15) 1.05453(14) 0.26779(12) 0.0258(4) Uiso 1.000000 R
C39 C 0.48496(16) 0.80964(16) 0.08789(13) 0.0264(3) Uani 1.000000 .
H39a H 0.42117(16) 0.78961(16) 0.02240(13) 0.0317(4) Uiso 1.000000 R
H39b H 0.55829(16) 0.91449(16) 0.12027(13) 0.0317(4) Uiso 1.000000 R
C46 C -0.16851(18) 0.18661(16) 0.12676(14) 0.0310(4) Uani 1.000000 .
H46a H -0.17774(18) 0.18585(16) 0.19928(14) 0.0372(4) Uiso 1.000000 R
H46b H -0.26413(18) 0.11866(16) 0.07594(14) 0.0372(4) Uiso 1.000000 R
C13 C -0.10773(15) 0.64327(16) 0.35839(12) 0.0250(3) Uani 1.000000 .
H13a H -0.16899(15) 0.62473(16) 0.29217(12) 0.0300(4) Uiso 1.000000 R
H13b H -0.14048(15) 0.54912(16) 0.36375(12) 0.0300(4) Uiso 1.000000 R
C43 C 0.48639(17) 0.79611(18) 0.27423(14) 0.0293(3) Uani 1.000000 .
H43a H 0.55947(17) 0.90039(18) 0.31594(14) 0.0351(4) Uiso 1.000000 R
H43b H 0.42358(17) 0.76727(18) 0.32329(14) 0.0351(4) Uiso 1.000000 R
C45 C -0.12017(15) 0.34524(15) 0.13801(12) 0.0229(3) Uani 1.000000 .
H45a H -0.19191(15) 0.37709(15) 0.16611(12) 0.0275(4) Uiso 1.000000 R
H45b H -0.11477(15) 0.34560(15) 0.06509(12) 0.0275(4) Uiso 1.000000 R
C16 C -0.12354(18) 0.75646(18) 0.46241(13) 0.0336(4) Uani 1.000000 .
H16a H -0.09719(18) 0.84802(18) 0.45430(13) 0.0403(4) Uiso 1.000000 R
H16b H -0.22530(18) 0.71608(18) 0.46897(13) 0.0403(4) Uiso 1.000000 R
C17 C 0.15060(17) 0.73616(17) 0.45313(12) 0.0288(3) Uani 1.000000 .
H17a H 0.12425(17) 0.64326(17) 0.45913(12) 0.0345(4) Uiso 1.000000 R
H17b H 0.25259(17) 0.77773(17) 0.44721(12) 0.0345(4) Uiso 1.000000 R
C1 C 0.48832(19) 1.35520(16) 0.36507(15) 0.0346(4) Uani 1.000000 .
H1a H 0.39154(19) 1.34895(16) 0.36101(15) 0.0415(5) Uiso 1.000000 R
H1b H 0.56096(19) 1.46032(16) 0.40099(15) 0.0415(5) Uiso 1.000000 R
C5 C 0.40054(17) 1.11512(15) 0.18876(13) 0.0266(3) Uani 1.000000 .
H5a H 0.42056(17) 1.07090(15) 0.11609(13) 0.0320(4) Uiso 1.000000 R
H5b H 0.30086(17) 1.10056(15) 0.17716(13) 0.0320(4) Uiso 1.000000 R
C3 C 0.39536(17) 1.10991(16) 0.37836(13) 0.0273(3) Uani 1.000000 .
H3a H 0.29573(17) 1.09603(16) 0.37541(13) 0.0328(4) Uiso 1.000000 R
H3b H 0.41118(17) 1.06184(16) 0.42204(13) 0.0328(4) Uiso 1.000000 R
C49 C 0.14326(16) 0.40312(16) 0.17422(13) 0.0263(3) Uani 1.000000 .
H49a H 0.15590(16) 0.41012(16) 0.10392(13) 0.0315(4) Uiso 1.000000 R
H49b H 0.23734(16) 0.46936(16) 0.22723(13) 0.0315(4) Uiso 1.000000 R
C48 C 0.09539(19) 0.24136(17) 0.15584(14) 0.0320(4) Uani 1.000000 .
H48a H 0.16437(19) 0.21006(17) 0.12071(14) 0.0385(4) Uiso 1.000000 R
H48b H 0.09836(19) 0.23788(17) 0.22790(14) 0.0385(4) Uiso 1.000000 R
C2 C 0.50461(18) 1.27741(17) 0.43438(14) 0.0332(4) Uani 1.000000 .
H2a H 0.60403(18) 1.29073(17) 0.44346(14) 0.0398(4) Uiso 1.000000 R
H2b H 0.48802(18) 1.32288(17) 0.50821(14) 0.0398(4) Uiso 1.000000 R
C6 C 0.50868(18) 1.28297(16) 0.24736(14) 0.0343(4) Uani 1.000000 .
H6a H 0.49407(18) 1.33169(16) 0.20380(14) 0.0411(5) Uiso 1.000000 R
H6b H 0.60849(18) 1.29726(16) 0.25127(14) 0.0411(5) Uiso 1.000000 R
C40 C 0.56134(18) 0.71181(18) 0.05271(15) 0.0357(4) Uani 1.000000 .
H40a H 0.48780(18) 0.60750(18) 0.01217(15) 0.0428(5) Uiso 1.000000 R
H40b H 0.62353(18) 0.73871(18) 0.00275(15) 0.0428(5) Uiso 1.000000 R
C41 C 0.65426(18) 0.7308(2) 0.15358(16) 0.0405(4) Uani 1.000000 .
H41a H 0.69625(18) 0.6630(2) 0.12889(16) 0.0486(5) Uiso 1.000000 R
H41b H 0.73454(18) 0.8325(2) 0.18935(16) 0.0486(5) Uiso 1.000000 R
C42 C 0.56345(19) 0.6989(2) 0.23750(16) 0.0387(4) Uani 1.000000 .
H42a H 0.62688(19) 0.7178(2) 0.30271(16) 0.0465(5) Uiso 1.000000 R
H42b H 0.49022(19) 0.5940(2) 0.20429(16) 0.0465(5) Uiso 1.000000 R
C47 C -0.05864(19) 0.13270(16) 0.08291(14) 0.0344(4) Uani 1.000000 .
H47a H -0.08868(19) 0.03493(16) 0.08129(14) 0.0412(5) Uiso 1.000000 R
H47b H -0.05787(19) 0.12237(16) 0.00688(14) 0.0412(5) Uiso 1.000000 R
C30 C -0.0261(2) 0.79221(19) 0.56813(13) 0.0379(4) Uani 1.000000 .
H30a H -0.0337(2) 0.86909(19) 0.63175(13) 0.0455(5) Uiso 1.000000 R
H30b H -0.0598(2) 0.70321(19) 0.58111(13) 0.0455(5) Uiso 1.000000 R
C50 C 0.13342(18) 0.84629(18) 0.55826(13) 0.0351(4) Uani 1.000000 .
H50a H 0.19138(18) 0.85946(18) 0.62381(13) 0.0421(5) Uiso 1.000000 R
H50b H 0.17104(18) 0.94291(18) 0.55627(13) 0.0421(5) Uiso 1.000000 R
O1 O 0.11171(10) 0.89613(10) 0.20161(9) 0.0242(2) Uani 1.000000 .
O2 O -0.07229(10) 0.61810(11) 0.10889(8) 0.0238(2) Uani 1.000000 .
H2 H -0.07067(10) 0.63927(11) 0.05570(8) 0.0285(3) Uiso 1.000000 R
C52 C 0.17276(14) 0.81703(14) 0.18696(11) 0.0184(3) Uani 1.000000 .
C51 C 0.07126(14) 0.64680(14) 0.15121(11) 0.0177(3) Uani 1.000000 .
H51 H 0.10347(14) 0.58885(14) 0.09054(11) 0.0212(3) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C4 N1 C38 117.15(10) . . ?
C52 N1 C38 123.58(10) . . ?
C52 N1 C4 119.26(11) . . ?
C44 N2 C0AA 116.49(10) . . ?
C51 N2 C0AA 115.60(10) . . ?
C51 N2 C44 115.63(10) . . ?
C13 C0AA N2 116.74(11) . . ?
C17 C0AA N2 111.38(11) . . ?
C17 C0AA C13 109.79(12) . . ?
C45 C44 N2 115.78(11) . . ?
C49 C44 N2 111.16(11) . . ?
C49 C44 C45 109.46(11) . . ?
C39 C38 N1 110.50(11) . . ?
C43 C38 N1 112.42(12) . . ?
C43 C38 C39 111.78(12) . . ?
C5 C4 N1 113.56(11) . . ?
C3 C4 N1 111.88(11) . . ?
C3 C4 C5 112.15(12) . . ?
C40 C39 C38 111.07(12) . . ?
C47 C46 C45 111.21(12) . . ?
C16 C13 C0AA 110.13(12) . . ?
C42 C43 C38 111.04(13) . . ?
C46 C45 C44 110.08(12) . . ?
C30 C16 C13 111.50(14) . . ?
C50 C17 C0AA 111.23(13) . . ?
C6 C1 C2 110.70(13) . . ?
C6 C5 C4 110.11(13) . . ?
C2 C3 C4 110.10(12) . . ?
C48 C49 C44 111.87(12) . . ?
C47 C48 C49 112.36(13) . . ?
C3 C2 C1 111.15(13) . . ?
C5 C6 C1 111.53(12) . . ?
C41 C40 C39 111.45(14) . . ?
C42 C41 C40 111.26(13) . . ?
C41 C42 C43 111.81(14) . . ?
C48 C47 C46 111.33(13) . . ?
C50 C30 C16 111.05(13) . . ?
C30 C50 C17 111.92(13) . . ?
O1 C52 N1 122.97(12) . . ?
C51 C52 N1 120.15(11) . . ?
C51 C52 O1 116.79(11) . . ?
O2 C51 N2 115.45(10) . . ?
C52 C51 N2 109.01(10) . . ?
C52 C51 O2 105.54(10) . . ?
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
N1 C38 1.4796(17) . ?
N1 C4 1.4848(16) . ?
N1 C52 1.3463(17) . ?
N2 C0AA 1.4746(17) . ?
N2 C44 1.4789(16) . ?
N2 C51 1.4411(17) . ?
C0AA C13 1.5353(19) . ?
C0AA C17 1.527(2) . ?
C44 C45 1.5333(19) . ?
C44 C49 1.530(2) . ?
C38 C39 1.529(2) . ?
C38 C43 1.524(2) . ?
C4 C5 1.528(2) . ?
C4 C3 1.527(2) . ?
C39 C40 1.530(2) . ?
C46 C45 1.5315(19) . ?
C46 C47 1.519(2) . ?
C13 C16 1.529(2) . ?
C43 C42 1.532(2) . ?
C16 C30 1.520(2) . ?
C17 C50 1.528(2) . ?
C1 C2 1.520(2) . ?
C1 C6 1.521(2) . ?
C5 C6 1.5308(19) . ?
C3 C2 1.530(2) . ?
C49 C48 1.535(2) . ?
C48 C47 1.521(2) . ?
C40 C41 1.520(3) . ?
C41 C42 1.515(3) . ?
C30 C50 1.520(2) . ?
O1 C52 1.2362(16) . ?
O2 C51 1.4278(16) . ?
C52 C51 1.5585(17) . ?
