#------------------------------------------------------------------------------
#$Date: 2020-10-06 10:14:07 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557708.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_1557708
loop_
_publ_author_name
'Zheng, Shuai'
'Zhang, Shuo-Qing'
'Saeednia, Borna'
'Zhou, Jiawang'
'Anna, Jessica M.'
'Hong, Xin'
'Molander, Gary A.'
_publ_section_title
;
 Diastereoselective olefin amidoacylation via photoredox PCET/nickel-dual
 catalysis: reaction scope and mechanistic insights
;
_journal_issue                   16
_journal_name_full               'Chemical Science'
_journal_page_first              4131
_journal_page_last               4137
_journal_paper_doi               10.1039/D0SC01459A
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_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             2020-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-04 deposited with the CCDC.	2020-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.266(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8161(6)
_cell_length_b                   8.4185(5)
_cell_length_c                   16.7407(11)
_cell_measurement_reflns_used    9013
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.399
_cell_measurement_theta_min      3.076
_cell_volume                     1512.09(16)
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       'Bruker APEX3 v2018.7-2'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CMOS area detector'
_diffrn_measurement_device_type  'Bruker D8QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23261
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.398
_diffrn_reflns_theta_min         2.906
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2016/2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       bar
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0379
_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)+(0.0418P)²+0.7109P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0944
_reflns_number_gt                2437
_reflns_number_total             2783
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc01459a2.cif
_cod_data_source_block           9243
_cod_depositor_comments
;Adding full bibliography for 1557708.cif.

 Adding full bibliography for 1557708.cif.
;
_cod_database_code               1557708
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.967
_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 0.06380(9) -0.07155(11) 0.60249(6) 0.0194(2) Uani 1 1 d . . . . .
O2 O 0.51763(9) 0.22534(12) 0.43126(6) 0.0225(3) Uani 1 1 d . . . . .
N1 N 0.16881(10) 0.13864(13) 0.55386(6) 0.0118(2) Uani 1 1 d . . . . .
C1 C 0.13631(12) 0.25687(15) 0.60816(8) 0.0115(3) Uani 1 1 d . . . . .
C2 C 0.13958(12) 0.22189(17) 0.68976(8) 0.0144(3) Uani 1 1 d . . . . .
H2 H 0.161806 0.118342 0.709075 0.017 Uiso 1 1 calc R . . . .
C3 C 0.11032(13) 0.33855(17) 0.74265(8) 0.0170(3) Uani 1 1 d . . . . .
H3 H 0.110378 0.313565 0.797994 0.020 Uiso 1 1 calc R . . . .
C4 C 0.08092(12) 0.49150(17) 0.71571(9) 0.0178(3) Uani 1 1 d . . . . .
H4 H 0.062530 0.571352 0.752532 0.021 Uiso 1 1 calc R . . . .
C5 C 0.07861(12) 0.52689(17) 0.63457(9) 0.0172(3) Uani 1 1 d . . . . .
H5 H 0.059158 0.631532 0.615775 0.021 Uiso 1 1 calc R . . . .
C6 C 0.10469(12) 0.40954(16) 0.58076(8) 0.0142(3) Uani 1 1 d . . . . .
H6 H 0.100926 0.433558 0.525056 0.017 Uiso 1 1 calc R . . . .
C7 C 0.13106(12) -0.01683(16) 0.55577(8) 0.0140(3) Uani 1 1 d . . . . .
C8 C 0.18365(13) -0.10607(17) 0.48976(9) 0.0190(3) Uani 1 1 d . . . . .
H8a H 0.115607 -0.148742 0.450508 0.023 Uiso 1 1 calc R . . . .
H8b H 0.236117 -0.195636 0.512427 0.023 Uiso 1 1 calc R . . . .
C9 C 0.26135(13) 0.01284(17) 0.44933(8) 0.0173(3) Uani 1 1 d . . . . .
H9a H 0.237410 0.011857 0.390260 0.021 Uiso 1 1 calc R . . . .
H9b H 0.351064 -0.013296 0.460917 0.021 Uiso 1 1 calc R . . . .
C10 C 0.23470(12) 0.17740(16) 0.48448(8) 0.0123(3) Uani 1 1 d . . . . .
H10 H 0.177834 0.238695 0.443915 0.015 Uiso 1 1 calc R . . . .
C11 C 0.35383(12) 0.27696(16) 0.51099(8) 0.0133(3) Uani 1 1 d . . . . .
H11 H 0.327025 0.383191 0.529271 0.016 Uiso 1 1 calc R . . . .
C12 C 0.42437(12) 0.30302(16) 0.43860(8) 0.0148(3) Uani 1 1 d . . . . .
C13 C 0.37937(12) 0.42547(16) 0.37645(8) 0.0143(3) Uani 1 1 d . . . . .
C14 C 0.44618(14) 0.44601(17) 0.31083(8) 0.0182(3) Uani 1 1 d . . . . .
H14 H 0.517095 0.381724 0.306166 0.022 Uiso 1 1 calc R . . . .
C15 C 0.40956(14) 0.55963(17) 0.25256(9) 0.0207(3) Uani 1 1 d . . . . .
H15 H 0.455850 0.573398 0.208464 0.025 Uiso 1 1 calc R . . . .
C16 C 0.30551(14) 0.65316(17) 0.25853(8) 0.0192(3) Uani 1 1 d . . . . .
H16 H 0.280296 0.730496 0.218438 0.023 Uiso 1 1 calc R . . . .
C17 C 0.23831(13) 0.63350(17) 0.32325(9) 0.0183(3) Uani 1 1 d . . . . .
H17 H 0.166822 0.697124 0.327273 0.022 Uiso 1 1 calc R . . . .
C18 C 0.27543(12) 0.52106(16) 0.38205(8) 0.0149(3) Uani 1 1 d . . . . .
H18 H 0.229656 0.509061 0.426505 0.018 Uiso 1 1 calc R . . . .
C19 C 0.43602(13) 0.19984(17) 0.58123(8) 0.0168(3) Uani 1 1 d . . . . .
H19a H 0.394895 0.207246 0.630010 0.025 Uiso 1 1 calc GR . . . .
H19b H 0.516439 0.254867 0.589974 0.025 Uiso 1 1 calc GR . . . .
H19c H 0.449495 0.087882 0.568815 0.025 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
C1 N1 C10 122.15(11) . . ?
C7 N1 C1 123.66(11) . . ?
C7 N1 C10 113.85(11) . . ?
C2 C1 N1 120.07(12) . . ?
C6 C1 N1 120.39(12) . . ?
C6 C1 C2 119.51(12) . . ?
C3 C2 C1 119.81(13) . . ?
C2 C3 C4 120.76(13) . . ?
C5 C4 C3 119.49(13) . . ?
C4 C5 C6 120.12(13) . . ?
C5 C6 C1 120.27(13) . . ?
O1 C7 N1 125.21(13) . . ?
O1 C7 C8 126.26(13) . . ?
N1 C7 C8 108.51(11) . . ?
C7 C8 C9 106.24(11) . . ?
C8 C9 C10 106.29(11) . . ?
N1 C10 C9 103.50(10) . . ?
N1 C10 C11 111.12(10) . . ?
C9 C10 C11 113.84(11) . . ?
C12 C11 C10 109.28(10) . . ?
C19 C11 C10 111.82(11) . . ?
C19 C11 C12 111.82(11) . . ?
O2 C12 C11 120.31(12) . . ?
O2 C12 C13 119.83(12) . . ?
C13 C12 C11 119.85(11) . . ?
C14 C13 C12 118.32(12) . . ?
C18 C13 C12 122.87(12) . . ?
C18 C13 C14 118.80(13) . . ?
C15 C14 C13 120.47(13) . . ?
C16 C15 C14 120.16(13) . . ?
C15 C16 C17 119.87(13) . . ?
C18 C17 C16 120.10(14) . . ?
C17 C18 C13 120.60(13) . . ?
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 C7 1.2236(17) . ?
O2 C12 1.2213(17) . ?
N1 C1 1.4216(17) . ?
N1 C7 1.3726(18) . ?
N1 C10 1.4741(16) . ?
C1 C2 1.3936(19) . ?
C1 C6 1.3927(19) . ?
C2 C3 1.385(2) . ?
C3 C4 1.388(2) . ?
C4 C5 1.388(2) . ?
C5 C6 1.3897(19) . ?
C7 C8 1.5061(19) . ?
C8 C9 1.520(2) . ?
C9 C10 1.5464(18) . ?
C10 C11 1.5541(18) . ?
C11 C12 1.5273(18) . ?
C11 C19 1.5266(18) . ?
C12 C13 1.5013(19) . ?
C13 C14 1.3998(19) . ?
C13 C18 1.3953(19) . ?
C14 C15 1.388(2) . ?
C15 C16 1.387(2) . ?
C16 C17 1.389(2) . ?
C17 C18 1.388(2) . ?
