#------------------------------------------------------------------------------
#$Date: 2020-11-04 03:24:43 +0200 (Wed, 04 Nov 2020) $
#$Revision: 258712 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/52/4135281.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_4135281
loop_
_publ_author_name
'Yao, Qi-Jun'
'Xie, Pei-Pei'
'Wu, Yong-Jie'
'Feng, Ya-Lan'
'Teng, Ming-Ya'
'Hong, Xin'
'Shi, Bing-Feng'
_publ_section_title
;
 Enantioselective Synthesis of Atropisomeric Anilides via Pd(II)-Catalyzed
 Asymmetric C-H Olefination.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18266
_journal_page_last               18276
_journal_paper_doi               10.1021/jacs.0c09400
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H26 N2 O5'
_chemical_formula_sum            'C31 H26 N2 O5'
_chemical_formula_weight         506.54
_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     dual
_audit_creation_date             2019-04-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.2170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7185(2)
_cell_length_b                   19.1801(6)
_cell_length_c                   8.9140(3)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      5.00
_cell_volume                     1309.19(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12760
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.205
_diffrn_reflns_theta_min         4.611
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1391 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.8457.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.244
_refine_diff_density_max         0.109
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2243 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0287
_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)+(0.0398P)²+0.1866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0732
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                4726
_reflns_number_total             4734
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c09400_si_003.cif
_cod_data_source_block           190401_yqj_h_103_5_2_0m
_cod_depositor_comments
'Adding full bibliography for 4135280--4135281.cif.'
_cod_database_code               4135281
_shelx_shelxl_version_number     2016/6
_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   0.845
_shelx_estimated_absorpt_t_min   0.714
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25),
  C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C31(H31A,H31B,H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
O1 O 0.31923(17) 0.45399(8) 0.42777(15) 0.0348(3) Uani 1 1 d . . . . .
O2 O 0.5377(2) 0.30244(8) 0.80859(17) 0.0395(3) Uani 1 1 d . . . . .
O3 O 0.6967(3) 0.29637(9) 1.0356(2) 0.0529(5) Uani 1 1 d . . . . .
O4 O 0.1355(2) 0.64044(8) 0.19996(18) 0.0408(4) Uani 1 1 d . . . . .
O5 O -0.0158(2) 0.71684(9) 0.32203(18) 0.0430(4) Uani 1 1 d . . . . .
N1 N 0.7157(2) 0.52600(9) 0.3818(2) 0.0331(4) Uani 1 1 d . . . . .
N2 N 0.45071(18) 0.53580(7) 0.58663(16) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.8633(3) 0.51069(12) 0.3238(3) 0.0394(5) Uani 1 1 d . . . . .
H1 H 0.932328 0.548368 0.295712 0.047 Uiso 1 1 calc R . . . .
C2 C 0.9211(3) 0.44435(12) 0.3025(2) 0.0370(5) Uani 1 1 d . . . . .
H2 H 1.028922 0.436540 0.264304 0.044 Uiso 1 1 calc R . . . .
C3 C 0.8199(3) 0.38953(13) 0.3376(3) 0.0482(6) Uani 1 1 d . . . . .
H3 H 0.855505 0.342844 0.323281 0.058 Uiso 1 1 calc R . . . .
C4 C 0.6650(3) 0.40347(11) 0.3940(3) 0.0427(5) Uani 1 1 d . . . . .
H4 H 0.590628 0.366569 0.417169 0.051 Uiso 1 1 calc R . . . .
C5 C 0.6202(2) 0.47202(9) 0.41630(19) 0.0240(4) Uani 1 1 d . . . . .
C6 C 0.4509(2) 0.48638(9) 0.47754(19) 0.0236(4) Uani 1 1 d . . . . .
C7 C 0.2844(2) 0.54948(10) 0.6498(2) 0.0250(4) Uani 1 1 d . . . . .
H7A H 0.185285 0.543351 0.568896 0.030 Uiso 1 1 calc R . . . .
H7B H 0.283401 0.598433 0.684876 0.030 Uiso 1 1 calc R . . . .
C8 C 0.2603(2) 0.50165(10) 0.7795(2) 0.0288(4) Uani 1 1 d . . . . .
C9 C 0.1821(4) 0.43708(12) 0.7527(3) 0.0515(6) Uani 1 1 d . . . . .
H9 H 0.136810 0.423844 0.652744 0.062 Uiso 1 1 calc R . . . .
C10 C 0.1701(6) 0.39211(16) 0.8716(6) 0.0936(16) Uani 1 1 d . . . . .
H10 H 0.117142 0.347701 0.853402 0.112 Uiso 1 1 calc R . . . .
C11 C 0.2350(6) 0.4114(2) 1.0172(5) 0.0987(17) Uani 1 1 d . . . . .
H11 H 0.229601 0.379686 1.098365 0.118 Uiso 1 1 calc R . . . .
C12 C 0.3069(5) 0.4760(2) 1.0450(3) 0.0763(12) Uani 1 1 d . . . . .
H12 H 0.347756 0.489642 1.145679 0.092 Uiso 1 1 calc R . . . .
C13 C 0.3204(3) 0.52160(14) 0.9262(2) 0.0426(5) Uani 1 1 d . . . . .
H13 H 0.370679 0.566419 0.945416 0.051 Uiso 1 1 calc R . . . .
C14 C 0.6082(2) 0.56079(9) 0.67344(19) 0.0217(3) Uani 1 1 d . . . . .
C15 C 0.7021(2) 0.51618(9) 0.77646(19) 0.0236(3) Uani 1 1 d . . . . .
C16 C 0.8515(2) 0.54267(10) 0.8686(2) 0.0271(4) Uani 1 1 d . . . . .
H16 H 0.918538 0.512349 0.937407 0.033 Uiso 1 1 calc R . . . .
C17 C 0.8998(3) 0.61023(10) 0.8601(2) 0.0291(4) Uani 1 1 d . . . . .
H17 H 0.998487 0.626735 0.924779 0.035 Uiso 1 1 calc R . . . .
C18 C 0.8055(2) 0.65700(10) 0.7561(2) 0.0260(4) Uani 1 1 d . . . . .
C19 C 0.6578(2) 0.63203(9) 0.65788(19) 0.0227(3) Uani 1 1 d . . . . .
C20 C 0.5696(2) 0.68023(9) 0.5509(2) 0.0248(4) Uani 1 1 d . . . . .
C21 C 0.6274(3) 0.74834(10) 0.5488(2) 0.0309(4) Uani 1 1 d . . . . .
H21 H 0.568342 0.779921 0.477763 0.037 Uiso 1 1 calc R . . . .
C22 C 0.7705(3) 0.77243(10) 0.6482(2) 0.0339(4) Uani 1 1 d . . . . .
H22 H 0.806182 0.819745 0.644860 0.041 Uiso 1 1 calc R . . . .
C23 C 0.8579(3) 0.72754(10) 0.7493(2) 0.0317(4) Uani 1 1 d . . . . .
H23 H 0.955087 0.743785 0.816149 0.038 Uiso 1 1 calc R . . . .
C24 C 0.6486(2) 0.44352(9) 0.7926(2) 0.0239(4) Uani 1 1 d . . . . .
H24 H 0.560646 0.426124 0.717785 0.029 Uiso 1 1 calc R . . . .
C25 C 0.7109(3) 0.39953(11) 0.9014(2) 0.0352(4) Uani 1 1 d . . . . .
H25 H 0.802581 0.413681 0.976395 0.042 Uiso 1 1 calc R . . . .
C26 C 0.6376(3) 0.32910(10) 0.9055(2) 0.0299(4) Uani 1 1 d . . . . .
C27 C 0.6214(4) 0.22875(13) 1.0558(3) 0.0530(6) Uani 1 1 d . . . . .
H27A H 0.643208 0.198130 0.972148 0.080 Uiso 1 1 calc GR . . . .
H27B H 0.495201 0.233600 1.057248 0.080 Uiso 1 1 calc GR . . . .
H27C H 0.674481 0.208549 1.151637 0.080 Uiso 1 1 calc GR . . . .
C28 C 0.4206(2) 0.66186(9) 0.43652(19) 0.0252(4) Uani 1 1 d . . . . .
H28 H 0.432162 0.623481 0.371138 0.030 Uiso 1 1 calc R . . . .
C29 C 0.2715(3) 0.69715(10) 0.4221(2) 0.0299(4) Uani 1 1 d . . . . .
H29 H 0.256731 0.733780 0.491117 0.036 Uiso 1 1 calc R . . . .
C30 C 0.1282(3) 0.68098(10) 0.3019(2) 0.0302(4) Uani 1 1 d . . . . .
C31 C -0.1695(3) 0.70308(14) 0.2156(3) 0.0484(6) Uani 1 1 d . . . . .
H31A H -0.141643 0.709885 0.112281 0.073 Uiso 1 1 calc GR . . . .
H31B H -0.263123 0.735138 0.234672 0.073 Uiso 1 1 calc GR . . . .
H31C H -0.207743 0.654913 0.227631 0.073 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C26 O3 C27 115.36(18) . . ?
C30 O5 C31 116.40(18) . . ?
C5 N1 C1 116.17(17) . . ?
C6 N2 C7 118.19(14) . . ?
C6 N2 C14 122.73(14) . . ?
C14 N2 C7 116.65(14) . . ?
N1 C1 H1 117.8 . . ?
N1 C1 C2 124.3(2) . . ?
C2 C1 H1 117.8 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.7(2) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 123.55(18) . . ?
N1 C5 C6 118.27(16) . . ?
C4 C5 C6 118.14(17) . . ?
O1 C6 N2 122.50(17) . . ?
O1 C6 C5 119.65(16) . . ?
N2 C6 C5 117.85(14) . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
N2 C7 C8 112.25(14) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
C9 C8 C7 120.3(2) . . ?
C13 C8 C7 119.85(19) . . ?
C13 C8 C9 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.1(3) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 119.9(3) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 N2 119.03(15) . . ?
C15 C14 C19 121.89(16) . . ?
C19 C14 N2 118.97(15) . . ?
C14 C15 C16 118.61(16) . . ?
C14 C15 C24 121.34(15) . . ?
C16 C15 C24 120.05(15) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.24(17) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.22(17) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 119.40(17) . . ?
C23 C18 C17 120.35(17) . . ?
C23 C18 C19 120.26(16) . . ?
C14 C19 C20 124.67(16) . . ?
C18 C19 C14 117.58(16) . . ?
C18 C19 C20 117.75(16) . . ?
C19 C20 C28 124.48(16) . . ?
C21 C20 C19 119.42(16) . . ?
C21 C20 C28 116.07(16) . . ?
C20 C21 H21 118.9 . . ?
C20 C21 C22 122.13(17) . . ?
C22 C21 H21 118.9 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.63(17) . . ?
C23 C22 H22 120.2 . . ?
C18 C23 H23 119.6 . . ?
C22 C23 C18 120.80(18) . . ?
C22 C23 H23 119.6 . . ?
C15 C24 H24 116.8 . . ?
C25 C24 C15 126.47(16) . . ?
C25 C24 H24 116.8 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.82(17) . . ?
C26 C25 H25 120.1 . . ?
O2 C26 O3 122.66(18) . . ?
O2 C26 C25 126.21(18) . . ?
O3 C26 C25 111.13(17) . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C28 H28 118.8 . . ?
C29 C28 C20 122.31(16) . . ?
C29 C28 H28 118.8 . . ?
C28 C29 H29 119.1 . . ?
C28 C29 C30 121.71(18) . . ?
C30 C29 H29 119.1 . . ?
O4 C30 O5 123.50(18) . . ?
O4 C30 C29 125.73(18) . . ?
O5 C30 C29 110.76(17) . . ?
O5 C31 H31A 109.5 . . ?
O5 C31 H31B 109.5 . . ?
O5 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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 C6 1.226(2) . ?
O2 C26 1.198(3) . ?
O3 C26 1.347(2) . ?
O3 C27 1.442(3) . ?
O4 C30 1.203(3) . ?
O5 C30 1.338(3) . ?
O5 C31 1.447(3) . ?
N1 C1 1.342(3) . ?
N1 C5 1.329(2) . ?
N2 C6 1.358(2) . ?
N2 C7 1.488(2) . ?
N2 C14 1.439(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.370(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.369(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(3) . ?
C5 C6 1.503(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.506(3) . ?
C8 C9 1.385(3) . ?
C8 C13 1.385(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.367(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(2) . ?
C14 C19 1.430(2) . ?
C15 C16 1.423(2) . ?
C15 C24 1.466(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.353(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.423(3) . ?
C18 C19 1.430(2) . ?
C18 C23 1.415(3) . ?
C19 C20 1.437(2) . ?
C20 C21 1.381(3) . ?
C20 C28 1.481(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.405(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.363(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.329(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.467(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28 0.9500 . ?
C28 C29 1.328(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.473(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
