#------------------------------------------------------------------------------
#$Date: 2022-10-07 03:48:28 +0300 (Fri, 07 Oct 2022) $
#$Revision: 278408 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/76/1567637.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_1567637
loop_
_publ_author_name
'Cooper, Phillippa'
'Dalling, Andrew G.'
'Farrar, Elliot H. E.'
'Aldhous, Timothy P.'
'Grélaud, Simon'
'Lester, Eleanor'
'Feron, Lyman J.'
'Kemmitt, Paul D.'
'Grayson, Matthew N.'
'Bower, John F.'
_publ_section_title
;
 Atom and step economical synthesis of acyclic quaternary centers via
 iridium-catalyzed hydroarylative cross-coupling of 1,1-disubstituted
 alkenes
;
_journal_issue                   37
_journal_name_full               'Chemical Science'
_journal_page_first              11183
_journal_page_last               11189
_journal_paper_doi               10.1039/D2SC02790A
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C20 H27 N O2'
_chemical_formula_sum            'C20 H27 N O2'
_chemical_formula_weight         313.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2022-04-05 deposited with the CCDC.	2022-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.7690(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.31820(10)
_cell_length_b                   39.6141(8)
_cell_length_c                   7.7124(2)
_cell_measurement_reflns_used    5375
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.89
_cell_volume                     1792.68(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      200(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            32572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.923
_diffrn_reflns_theta_min         2.056
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0707 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.8138. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.198
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         4287
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0550
_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/[σ²(Fo²)+(0.0349P)²+0.8402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3315
_reflns_number_total             4287
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc02790a2.cif
_cod_data_source_block           testm1
_cod_depositor_comments          'Adding full bibliography for 1567637.cif.'
_cod_database_code               1567637
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.969
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C),
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.72031(18) 0.31102(3) 0.84250(14) 0.0255(2) Uani 1 1 d . . . . .
O2 O 0.5229(2) 0.40981(3) 0.59643(17) 0.0418(3) Uani 1 1 d . . . . .
N1 N 0.8229(2) 0.42560(3) 0.85386(19) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.4245(3) 0.33144(4) 0.3513(2) 0.0277(3) Uani 1 1 d . . . . .
H1 H 0.417840 0.354329 0.385743 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2361(3) 0.31679(4) 0.2161(2) 0.0320(4) Uani 1 1 d . . . . .
H2 H 0.102331 0.329817 0.157083 0.038 Uiso 1 1 calc R . . . .
C3 C 0.2413(3) 0.28342(4) 0.1666(2) 0.0325(4) Uani 1 1 d . . . . .
H3 H 0.111158 0.273442 0.074735 0.039 Uiso 1 1 calc R . . . .
C4 C 0.4357(3) 0.26467(4) 0.2510(2) 0.0324(4) Uani 1 1 d . . . . .
H4 H 0.440264 0.241678 0.217522 0.039 Uiso 1 1 calc R . . . .
C5 C 0.6256(3) 0.27942(4) 0.3853(2) 0.0277(4) Uani 1 1 d . . . . .
H5 H 0.759357 0.266296 0.442709 0.033 Uiso 1 1 calc R . . . .
C6 C 0.6239(3) 0.31288(4) 0.43721(19) 0.0221(3) Uani 1 1 d . . . . .
C7 C 0.8279(3) 0.33009(4) 0.5889(2) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.8974(3) 0.36195(4) 0.5101(2) 0.0332(4) Uani 1 1 d . . . . .
H8A H 0.947957 0.355685 0.408694 0.050 Uiso 1 1 calc GR . . . .
H8B H 1.022048 0.373294 0.609244 0.050 Uiso 1 1 calc GR . . . .
H8C H 0.766519 0.377238 0.461949 0.050 Uiso 1 1 calc GR . . . .
C9 C 1.0369(3) 0.30683(5) 0.6624(2) 0.0347(4) Uani 1 1 d . . . . .
H9A H 0.997676 0.286438 0.715992 0.052 Uiso 1 1 calc GR . . . .
H9B H 1.161800 0.318674 0.758826 0.052 Uiso 1 1 calc GR . . . .
H9C H 1.084508 0.300541 0.559492 0.052 Uiso 1 1 calc GR . . . .
C10 C 0.7509(2) 0.33877(4) 0.7466(2) 0.0222(3) Uani 1 1 d . . . . .
C11 C 0.6931(3) 0.36700(4) 0.8178(2) 0.0237(3) Uani 1 1 d . . . . .
C12 C 0.6237(3) 0.35608(4) 0.9664(2) 0.0281(4) Uani 1 1 d . . . . .
H12 H 0.574538 0.370085 1.044186 0.034 Uiso 1 1 calc R . . . .
C13 C 0.6416(3) 0.32257(4) 0.9742(2) 0.0280(4) Uani 1 1 d . . . . .
H13 H 0.604678 0.308663 1.059307 0.034 Uiso 1 1 calc R . . . .
C14 C 0.6744(3) 0.40245(4) 0.7461(2) 0.0273(3) Uani 1 1 d . . . . .
C15 C 1.0087(3) 0.41695(4) 1.0326(2) 0.0345(4) Uani 1 1 d . . . . .
H15 H 1.002629 0.392004 1.050162 0.041 Uiso 1 1 calc R . . . .
C16 C 0.9757(4) 0.43383(6) 1.1974(3) 0.0487(5) Uani 1 1 d . . . . .
H16A H 0.983374 0.458386 1.185662 0.073 Uiso 1 1 calc GR . . . .
H16B H 1.095848 0.426422 1.313534 0.073 Uiso 1 1 calc GR . . . .
H16C H 0.826549 0.427570 1.199393 0.073 Uiso 1 1 calc GR . . . .
C17 C 1.2416(3) 0.42505(6) 1.0268(3) 0.0531(6) Uani 1 1 d . . . . .
H17A H 1.258074 0.413655 0.919721 0.080 Uiso 1 1 calc GR . . . .
H17B H 1.361036 0.417208 1.142282 0.080 Uiso 1 1 calc GR . . . .
H17C H 1.255630 0.449493 1.014727 0.080 Uiso 1 1 calc GR . . . .
C18 C 0.8057(3) 0.46109(4) 0.7907(3) 0.0357(4) Uani 1 1 d . . . . .
H18 H 0.928737 0.473745 0.889921 0.043 Uiso 1 1 calc R . . . .
C19 C 0.5824(4) 0.47731(5) 0.7758(3) 0.0527(6) Uani 1 1 d . . . . .
H19A H 0.456272 0.466091 0.677369 0.079 Uiso 1 1 calc GR . . . .
H19B H 0.584655 0.501288 0.745248 0.079 Uiso 1 1 calc GR . . . .
H19C H 0.561969 0.475043 0.895159 0.079 Uiso 1 1 calc GR . . . .
C20 C 0.8543(4) 0.46475(6) 0.6125(3) 0.0537(6) Uani 1 1 d . . . . .
H20A H 1.000893 0.454156 0.629830 0.081 Uiso 1 1 calc GR . . . .
H20B H 0.860138 0.488753 0.583865 0.081 Uiso 1 1 calc GR . . . .
H20C H 0.733099 0.453701 0.509200 0.081 Uiso 1 1 calc GR . . . .
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'
O O 0.0106 0.0060 '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
C13 O1 C10 107.11(12) . . ?
C14 N1 C15 122.93(14) . . ?
C14 N1 C18 119.49(14) . . ?
C18 N1 C15 117.56(13) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.58(15) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.51(15) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.70(15) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.88(16) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.34(15) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 118.75(14) . . ?
C5 C6 C1 117.99(14) . . ?
C5 C6 C7 123.23(14) . . ?
C8 C7 C6 110.18(12) . . ?
C8 C7 C9 107.88(14) . . ?
C9 C7 C6 112.18(13) . . ?
C10 C7 C6 106.46(12) . . ?
C10 C7 C8 110.93(13) . . ?
C10 C7 C9 109.22(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C7 113.74(13) . . ?
C11 C10 O1 109.18(13) . . ?
C11 C10 C7 137.02(14) . . ?
C10 C11 C12 106.42(14) . . ?
C10 C11 C14 128.37(14) . . ?
C12 C11 C14 124.81(14) . . ?
C11 C12 H12 126.6 . . ?
C13 C12 C11 106.86(14) . . ?
C13 C12 H12 126.6 . . ?
O1 C13 H13 124.8 . . ?
C12 C13 O1 110.42(14) . . ?
C12 C13 H13 124.8 . . ?
O2 C14 N1 122.41(15) . . ?
O2 C14 C11 119.74(14) . . ?
N1 C14 C11 117.82(14) . . ?
N1 C15 H15 107.3 . . ?
N1 C15 C16 111.71(15) . . ?
N1 C15 C17 111.38(16) . . ?
C16 C15 H15 107.3 . . ?
C16 C15 C17 111.47(16) . . ?
C17 C15 H15 107.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18 106.4 . . ?
N1 C18 C19 112.40(15) . . ?
N1 C18 C20 111.91(15) . . ?
C19 C18 H18 106.4 . . ?
C19 C18 C20 112.64(17) . . ?
C20 C18 H18 106.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C10 1.3781(18) . ?
O1 C13 1.3648(19) . ?
O2 C14 1.2306(19) . ?
N1 C14 1.354(2) . ?
N1 C15 1.481(2) . ?
N1 C18 1.479(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.386(2) . ?
C1 C6 1.396(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.375(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C6 C7 1.542(2) . ?
C7 C8 1.534(2) . ?
C7 C9 1.536(2) . ?
C7 C10 1.508(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.355(2) . ?
C11 C12 1.437(2) . ?
C11 C14 1.497(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.332(2) . ?
C13 H13 0.9500 . ?
C15 H15 1.0000 . ?
C15 C16 1.517(3) . ?
C15 C17 1.523(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 1.0000 . ?
C18 C19 1.515(3) . ?
C18 C20 1.522(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
