#------------------------------------------------------------------------------
#$Date: 2022-01-06 23:48:02 +0200 (Thu, 06 Jan 2022) $
#$Revision: 271866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061072.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_7061072
loop_
_publ_author_name
'Dayaker, Gandrath'
'Erb, William'
'Hedidi, Madani'
'Chevallier, Floris'
'Blot, Marielle'
'Gros, Philippe C.'
'Hilmersson, Göran'
'Roisnel, Thierry'
'Dorcet, Vincent'
'Bentabed-Ababsa, Ghenia'
'Mongin, Florence'
_publ_section_title
;
 Enantioselective deprotometalation of alkyl ferrocenecarboxylates using
 bimetallic bases
;
_journal_issue                   48
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              22579
_journal_page_last               22590
_journal_paper_doi               10.1039/D1NJ04526A
_journal_volume                  45
_journal_year                    2021
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H28 N, Cl'
_chemical_formula_sum            'C18 H28 Cl N'
_chemical_formula_weight         293.86
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-09-16 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.3930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2823(3)
_cell_length_b                   7.3708(2)
_cell_length_c                   11.7289(3)
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.40
_cell_measurement_wavelength     0.71073
_cell_volume                     858.04(4)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR97 (A. Altomare et al., 1999)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      -0.0508560
_diffrn_orient_matrix_UB_12      0.0979761
_diffrn_orient_matrix_UB_13      0.0170636
_diffrn_orient_matrix_UB_21      0.0381006
_diffrn_orient_matrix_UB_22      -0.0417264
_diffrn_orient_matrix_UB_23      0.0918727
_diffrn_orient_matrix_UB_31      0.0781890
_diffrn_orient_matrix_UB_32      0.0840588
_diffrn_orient_matrix_UB_33      0.0257165
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.397
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
Flack x determined using 1613 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3854
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0266
_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/[σ²(Fo²)+(0.0413P)²+0.0918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0717
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                3724
_reflns_number_total             3854
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1nj04526a2.cif
_cod_data_source_block           D9_179F2_HpinoSR
_cod_depositor_comments
'Adding full bibliography for 7061069--7061073.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7061072
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.63594(16) 0.8480(3) -0.08739(15) 0.0288(4) Uani 1 1 d . . . . .
H1A H 0.653612 0.970075 -0.108772 0.043 Uiso 1 1 calc R U . . .
H1B H 0.540186 0.836488 -0.112108 0.043 Uiso 1 1 calc R U . . .
H1C H 0.659649 0.757960 -0.134680 0.043 Uiso 1 1 calc R U . . .
C2 C 0.72083(16) 0.8157(3) 0.05844(15) 0.0227(3) Uani 1 1 d . . . . .
H2 H 0.707309 0.687197 0.077054 0.027 Uiso 1 1 calc R U . . .
C3 C 0.86948(15) 0.8443(3) 0.10494(15) 0.0255(3) Uani 1 1 d . . . . .
C4 C 0.9568(2) 0.6961(3) 0.15027(19) 0.0363(5) Uani 1 1 d . . . . .
H4 H 0.924347 0.580610 0.158760 0.044 Uiso 1 1 calc R U . . .
C5 C 1.0926(2) 0.7189(4) 0.1831(2) 0.0479(6) Uani 1 1 d . . . . .
H5 H 1.152422 0.618498 0.214177 0.058 Uiso 1 1 calc R U . . .
C6 C 1.1399(2) 0.8864(4) 0.1707(2) 0.0493(7) Uani 1 1 d . . . . .
H6 H 1.231774 0.900164 0.191654 0.059 Uiso 1 1 calc R U . . .
C7 C 1.0546(2) 1.0335(4) 0.1282(2) 0.0432(5) Uani 1 1 d . . . . .
H7 H 1.088136 1.148988 0.121395 0.052 Uiso 1 1 calc R U . . .
C8 C 0.91897(19) 1.0137(3) 0.09492(18) 0.0316(4) Uani 1 1 d . . . . .
H8 H 0.860345 1.115455 0.065455 0.038 Uiso 1 1 calc R U . . .
N9 N 0.66955(14) 0.93921(19) 0.12902(13) 0.0197(3) Uani 1 1 d . . . . .
H9A H 0.672300 1.055737 0.104752 0.024 Uiso 1 1 calc R U . . .
H9B H 0.581759 0.911392 0.102840 0.024 Uiso 1 1 calc R U . . .
C10 C 0.74636(17) 0.9287(2) 0.27501(15) 0.0208(3) Uani 1 1 d . . . . .
H10 H 0.840227 0.970823 0.301869 0.025 Uiso 1 1 calc R U . . .
C11 C 0.68561(19) 1.0616(2) 0.33574(16) 0.0238(4) Uani 1 1 d . . . . .
H11 H 0.585464 1.062861 0.280622 0.029 Uiso 1 1 calc R U . . .
C12 C 0.7385(3) 1.2540(3) 0.3425(2) 0.0387(5) Uani 1 1 d . . . . .
H12A H 0.693875 1.336301 0.375715 0.058 Uiso 1 1 calc R U . . .
H12B H 0.719766 1.293083 0.255652 0.058 Uiso 1 1 calc R U . . .
H12C H 0.835990 1.256154 0.400497 0.058 Uiso 1 1 calc R U . . .
C13 C 0.71920(19) 0.9951(3) 0.47202(16) 0.0273(4) Uani 1 1 d . . . . .
H13 H 0.707034 1.087792 0.527831 0.033 Uiso 1 1 calc R U . . .
C14 C 0.8592(2) 0.9008(3) 0.53493(18) 0.0319(4) Uani 1 1 d . . . . .
H14A H 0.902898 0.892324 0.630606 0.038 Uiso 1 1 calc R U . . .
H14B H 0.922075 0.948014 0.505276 0.038 Uiso 1 1 calc R U . . .
C15 C 0.7811(2) 0.7270(3) 0.46268(17) 0.0283(4) Uani 1 1 d . . . . .
H15 H 0.817185 0.610271 0.510157 0.034 Uiso 1 1 calc R U . . .
C16 C 0.7567(2) 0.7305(2) 0.32202(18) 0.0267(4) Uani 1 1 d . . . . .
H16A H 0.672325 0.664920 0.265336 0.032 Uiso 1 1 calc R U . . .
H16B H 0.831860 0.668452 0.316870 0.032 Uiso 1 1 calc R U . . .
C17 C 0.65644(19) 0.8058(3) 0.46984(16) 0.0280(4) Uani 1 1 d . . . . .
C18 C 0.5155(2) 0.7609(3) 0.3626(2) 0.0385(5) Uani 1 1 d . . . . .
H18A H 0.499679 0.630114 0.362496 0.058 Uiso 1 1 calc R U . . .
H18B H 0.507399 0.796664 0.278737 0.058 Uiso 1 1 calc R U . . .
H18C H 0.448821 0.826877 0.377638 0.058 Uiso 1 1 calc R U . . .
C19 C 0.6603(3) 0.7633(3) 0.5999(2) 0.0420(5) Uani 1 1 d . . . . .
H19A H 0.591814 0.835759 0.608021 0.063 Uiso 1 1 calc R U . . .
H19B H 0.749542 0.792999 0.671206 0.063 Uiso 1 1 calc R U . . .
H19C H 0.641894 0.634047 0.603500 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.36505(3) 0.83468(5) 0.00404(4) 0.02569(11) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N9 111.40(14) . . ?
C3 C2 C1 112.27(13) . . ?
N9 C2 C1 108.55(14) . . ?
C3 C2 H2 108.2 . . ?
N9 C2 H2 108.2 . . ?
C1 C2 H2 108.2 . . ?
C8 C3 C4 119.63(17) . . ?
C8 C3 C2 120.96(17) . . ?
C4 C3 C2 119.3(2) . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 120.25(19) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C3 C8 C7 120.0(2) . . ?
C3 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 N9 C2 115.19(12) . . ?
C10 N9 H9A 108.5 . . ?
C2 N9 H9A 108.5 . . ?
C10 N9 H9B 108.5 . . ?
C2 N9 H9B 108.5 . . ?
H9A N9 H9B 107.5 . . ?
N9 C10 C16 111.01(13) . . ?
N9 C10 C11 110.36(13) . . ?
C16 C10 C11 114.11(14) . . ?
N9 C10 H10 107.0 . . ?
C16 C10 H10 107.0 . . ?
C11 C10 H10 107.0 . . ?
C12 C11 C13 110.23(15) . . ?
C12 C11 C10 111.33(15) . . ?
C13 C11 C10 109.38(14) . . ?
C12 C11 H11 108.6 . . ?
C13 C11 H11 108.6 . . ?
C10 C11 H11 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 C14 109.20(15) . . ?
C11 C13 C17 112.52(14) . . ?
C14 C13 C17 87.64(14) . . ?
C11 C13 H13 114.8 . . ?
C14 C13 H13 114.8 . . ?
C17 C13 H13 114.8 . . ?
C13 C14 C15 85.70(13) . . ?
C13 C14 H14A 114.4 . . ?
C15 C14 H14A 114.4 . . ?
C13 C14 H14B 114.4 . . ?
C15 C14 H14B 114.4 . . ?
H14A C14 H14B 111.5 . . ?
C16 C15 C14 109.62(16) . . ?
C16 C15 C17 110.21(14) . . ?
C14 C15 C17 87.47(14) . . ?
C16 C15 H15 115.4 . . ?
C14 C15 H15 115.4 . . ?
C17 C15 H15 115.4 . . ?
C15 C16 C10 110.07(14) . . ?
C15 C16 H16A 109.6 . . ?
C10 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C10 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C19 107.52(17) . . ?
C18 C17 C13 119.73(16) . . ?
C19 C17 C13 111.56(16) . . ?
C18 C17 C15 119.25(16) . . ?
C19 C17 C15 112.13(15) . . ?
C13 C17 C15 85.42(14) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
C1 C2 1.530(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.511(2) . ?
C2 N9 1.518(2) . ?
C2 H2 1.0000 . ?
C3 C8 1.395(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.401(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N9 C10 1.509(2) . ?
N9 H9A 0.9100 . ?
N9 H9B 0.9100 . ?
C10 C16 1.546(2) . ?
C10 C11 1.550(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.526(3) . ?
C11 C13 1.537(2) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.553(3) . ?
C13 C17 1.559(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.558(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.538(2) . ?
C15 C17 1.560(3) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.522(3) . ?
C17 C19 1.538(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N9 C2 C3 C8 -59.39(19) . . . . ?
C1 C2 C3 C8 62.6(2) . . . . ?
N9 C2 C3 C4 125.03(17) . . . . ?
C1 C2 C3 C4 -112.99(19) . . . . ?
C8 C3 C4 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 174.64(16) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C4 C3 C8 C7 1.0(3) . . . . ?
C2 C3 C8 C7 -174.55(16) . . . . ?
C6 C7 C8 C3 0.1(3) . . . . ?
C3 C2 N9 C10 -53.81(18) . . . . ?
C1 C2 N9 C10 -177.92(14) . . . . ?
C2 N9 C10 C16 -52.99(19) . . . . ?
C2 N9 C10 C11 179.46(13) . . . . ?
N9 C10 C11 C12 -82.36(17) . . . . ?
C16 C10 C11 C12 151.83(16) . . . . ?
N9 C10 C11 C13 155.58(14) . . . . ?
C16 C10 C11 C13 29.8(2) . . . . ?
C12 C11 C13 C14 -89.53(19) . . . . ?
C10 C11 C13 C14 33.19(19) . . . . ?
C12 C11 C13 C17 174.89(16) . . . . ?
C10 C11 C13 C17 -62.39(19) . . . . ?
C11 C13 C14 C15 -85.48(16) . . . . ?
C17 C13 C14 C15 27.58(13) . . . . ?
C13 C14 C15 C16 83.00(16) . . . . ?
C13 C14 C15 C17 -27.57(13) . . . . ?
C14 C15 C16 C10 -29.4(2) . . . . ?
C17 C15 C16 C10 65.3(2) . . . . ?
N9 C10 C16 C15 -157.12(14) . . . . ?
C11 C10 C16 C15 -31.6(2) . . . . ?
C11 C13 C17 C18 -39.0(2) . . . . ?
C14 C13 C17 C18 -148.80(17) . . . . ?
C11 C13 C17 C19 -165.71(16) . . . . ?
C14 C13 C17 C19 84.46(17) . . . . ?
C11 C13 C17 C15 82.29(16) . . . . ?
C14 C13 C17 C15 -27.55(12) . . . . ?
C16 C15 C17 C18 39.2(2) . . . . ?
C14 C15 C17 C18 149.15(17) . . . . ?
C16 C15 C17 C19 166.05(17) . . . . ?
C14 C15 C17 C19 -83.96(18) . . . . ?
C16 C15 C17 C13 -82.52(16) . . . . ?
C14 C15 C17 C13 27.47(12) . . . . ?
