#------------------------------------------------------------------------------
#$Date: 2024-09-06 01:24:31 +0200 (Fri 06 de Sep de 2024) $
#$Revision: 294457 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/34/7133421.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_7133421
loop_
_publ_author_name
'Liu, Zi-Li'
'Wang, Yu-Xin'
'Yang, Zi-Qi'
'Yang, Yu-Heng'
'Liu, Yin-Ping'
'Hao, Wen-Juan'
'Jiang, Bo'
_publ_section_title
;
 Construction of central and axial chirality via
 Pd(II)/Bim-catalyzed asymmetric dearomative Michael reaction of
 polycyclic tropones.
;
_journal_issue                   67
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8908
_journal_page_last               8911
_journal_paper_doi               10.1039/d4cc03166k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_sum            'C27 H18 Br N O'
_chemical_formula_weight         452.33
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-06-27 deposited with the CCDC.	2024-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.151(6)
_cell_length_b                   12.057(9)
_cell_length_c                   19.765(15)
_cell_measurement_reflns_used    2931
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.373
_cell_measurement_theta_min      2.665
_cell_volume                     1942(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0731
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9149
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    2.136
_exptl_absorpt_correction_T_max  0.7687
_exptl_absorpt_correction_T_min  0.5666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0338P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                2471
_reflns_number_total             3430
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4cc03166k2.cif
_cod_data_source_block           230704b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7133421.cif.
;
_cod_original_cell_volume        1943(3)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7133421
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.05328(8) -0.32105(4) -0.05338(2) 0.0594(2) Uani 1 1 d . . .
N1 N 1.1482(4) 0.3316(3) 0.15772(16) 0.0373(9) Uani 1 1 d . . .
H1 H 1.1579 0.3966 0.1751 0.045 Uiso 1 1 calc R . .
O1 O 0.7737(4) 0.0735(3) 0.30560(17) 0.0580(10) Uani 1 1 d . . .
C1 C 1.2671(6) 0.2770(4) 0.1233(2) 0.0353(12) Uani 1 1 d . . .
C2 C 1.4240(6) 0.3105(4) 0.1087(2) 0.0409(11) Uani 1 1 d . . .
H2 H 1.4636 0.3789 0.1230 0.049 Uiso 1 1 calc R . .
C3 C 1.5188(6) 0.2398(4) 0.0724(2) 0.0452(13) Uani 1 1 d . . .
H3 H 1.6253 0.2606 0.0613 0.054 Uiso 1 1 calc R . .
C4 C 1.4610(6) 0.1377(4) 0.0516(2) 0.0509(13) Uani 1 1 d . . .
H4 H 1.5293 0.0912 0.0268 0.061 Uiso 1 1 calc R . .
C5 C 1.3067(6) 0.1039(4) 0.0667(2) 0.0443(13) Uani 1 1 d . . .
H5 H 1.2696 0.0349 0.0523 0.053 Uiso 1 1 calc R . .
C6 C 1.2040(5) 0.1731(4) 0.10393(19) 0.0332(10) Uani 1 1 d . . .
C7 C 1.0397(5) 0.1688(3) 0.12888(18) 0.0322(10) Uani 1 1 d . . .
C8 C 0.9163(6) 0.0791(3) 0.1298(2) 0.0345(11) Uani 1 1 d . . .
H8 H 0.8124 0.1110 0.1141 0.041 Uiso 1 1 calc R . .
C9 C 0.8896(6) 0.0388(4) 0.2020(2) 0.0418(13) Uani 1 1 d . . .
H9A H 0.8218 -0.0272 0.1998 0.050 Uiso 1 1 calc R . .
H9B H 0.9953 0.0163 0.2198 0.050 Uiso 1 1 calc R . .
C10 C 0.8137(6) 0.1153(4) 0.2521(2) 0.0368(11) Uani 1 1 d . . .
C11 C 0.7799(6) 0.2344(4) 0.2407(2) 0.0319(11) Uani 1 1 d . . .
C12 C 0.6559(6) 0.2784(4) 0.2816(2) 0.0395(12) Uani 1 1 d . . .
H12 H 0.5980 0.2312 0.3102 0.047 Uiso 1 1 calc R . .
C13 C 0.6182(6) 0.3866(4) 0.2809(2) 0.0397(12) Uani 1 1 d . . .
H13 H 0.5408 0.4140 0.3111 0.048 Uiso 1 1 calc R . .
C14 C 0.6941(6) 0.4591(4) 0.2349(2) 0.0342(11) Uani 1 1 d . . .
C15 C 0.6553(6) 0.5712(4) 0.2325(3) 0.0462(13) Uani 1 1 d . . .
H15 H 0.5818 0.6008 0.2637 0.055 Uiso 1 1 calc R . .
C16 C 0.7236(7) 0.6369(4) 0.1854(3) 0.0572(15) Uani 1 1 d . . .
H16 H 0.7030 0.7128 0.1859 0.069 Uiso 1 1 calc R . .
C17 C 0.8231(7) 0.5929(4) 0.1367(3) 0.0548(14) Uani 1 1 d . . .
H17 H 0.8604 0.6382 0.1019 0.066 Uiso 1 1 calc R . .
C18 C 0.8687(6) 0.4852(4) 0.1379(2) 0.0431(13) Uani 1 1 d . . .
H18 H 0.9390 0.4578 0.1048 0.052 Uiso 1 1 calc R . .
C19 C 0.8098(6) 0.4142(3) 0.1892(2) 0.0333(11) Uani 1 1 d . . .
C20 C 0.8623(5) 0.3025(3) 0.19636(19) 0.0291(10) Uani 1 1 d . . .
C21 C 1.0113(5) 0.2674(3) 0.1606(2) 0.0273(11) Uani 1 1 d . . .
C22 C 0.9566(6) -0.0177(3) 0.0836(2) 0.0349(10) Uani 1 1 d . . .
C23 C 1.0397(7) -0.1086(4) 0.1067(2) 0.0428(12) Uani 1 1 d . . .
H23 H 1.0751 -0.1099 0.1514 0.051 Uiso 1 1 calc R . .
C24 C 1.0725(6) -0.1981(3) 0.0659(2) 0.0444(12) Uani 1 1 d . . .
H24 H 1.1265 -0.2600 0.0830 0.053 Uiso 1 1 calc R . .
C25 C 1.0245(6) -0.1943(3) 0.0003(2) 0.0375(11) Uani 1 1 d . . .
C26 C 0.9464(6) -0.1019(4) -0.0253(2) 0.0421(12) Uani 1 1 d . . .
H26 H 0.9160 -0.0988 -0.0706 0.050 Uiso 1 1 calc R . .
C27 C 0.9145(6) -0.0153(4) 0.0169(2) 0.0410(12) Uani 1 1 d . . .
H27 H 0.8625 0.0473 -0.0003 0.049 Uiso 1 1 calc R . .
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'
Br Br -0.2901 2.4595 '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 C21 109.4(4) . . ?
C1 N1 H1 125.3 . . ?
C21 N1 H1 125.3 . . ?
N1 C1 C2 129.0(4) . . ?
N1 C1 C6 107.9(4) . . ?
C2 C1 C6 123.1(5) . . ?
C3 C2 C1 117.2(5) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.6(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.6(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 117.2(4) . . ?
C5 C6 C7 136.5(4) . . ?
C1 C6 C7 106.3(4) . . ?
C21 C7 C6 106.7(4) . . ?
C21 C7 C8 121.1(4) . . ?
C6 C7 C8 132.0(4) . . ?
C7 C8 C22 114.1(4) . . ?
C7 C8 C9 110.0(4) . . ?
C22 C8 C9 110.4(3) . . ?
C7 C8 H8 107.3 . . ?
C22 C8 H8 107.3 . . ?
C9 C8 H8 107.3 . . ?
C10 C9 C8 119.0(4) . . ?
C10 C9 H9A 107.6 . . ?
C8 C9 H9A 107.6 . . ?
C10 C9 H9B 107.6 . . ?
C8 C9 H9B 107.6 . . ?
H9A C9 H9B 107.0 . . ?
O1 C10 C11 119.0(4) . . ?
O1 C10 C9 115.7(4) . . ?
C11 C10 C9 125.4(4) . . ?
C20 C11 C12 119.7(4) . . ?
C20 C11 C10 125.8(4) . . ?
C12 C11 C10 114.5(4) . . ?
C13 C12 C11 121.9(4) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 120.8(5) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 121.8(5) . . ?
C15 C14 C19 120.2(4) . . ?
C13 C14 C19 118.0(4) . . ?
C16 C15 C14 120.2(5) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.3(5) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 121.7(5) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 120.1(5) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 117.0(4) . . ?
C18 C19 C20 123.0(4) . . ?
C14 C19 C20 120.0(4) . . ?
C11 C20 C19 118.8(4) . . ?
C11 C20 C21 122.6(4) . . ?
C19 C20 C21 118.3(4) . . ?
N1 C21 C7 109.7(4) . . ?
N1 C21 C20 122.4(4) . . ?
C7 C21 C20 127.8(4) . . ?
C27 C22 C23 117.7(4) . . ?
C27 C22 C8 120.7(4) . . ?
C23 C22 C8 121.6(4) . . ?
C22 C23 C24 122.1(4) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C25 C24 C23 118.6(4) . . ?
C25 C24 H24 120.7 . . ?
C23 C24 H24 120.7 . . ?
C24 C25 C26 120.7(4) . . ?
C24 C25 Br1 118.6(3) . . ?
C26 C25 Br1 120.6(3) . . ?
C27 C26 C25 118.9(4) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C26 C27 C22 121.9(4) . . ?
C26 C27 H27 119.1 . . ?
C22 C27 H27 119.1 . . ?
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
Br1 C25 1.874(4) . ?
N1 C1 1.356(5) . ?
N1 C21 1.359(5) . ?
N1 H1 0.8600 . ?
O1 C10 1.217(5) . ?
C1 C2 1.372(6) . ?
C1 C6 1.407(6) . ?
C2 C3 1.355(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.427(6) . ?
C7 C21 1.363(6) . ?
C7 C8 1.477(6) . ?
C8 C22 1.519(6) . ?
C8 C9 1.523(6) . ?
C8 H8 0.9800 . ?
C9 C10 1.488(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.480(6) . ?
C11 C20 1.376(6) . ?
C11 C12 1.399(6) . ?
C12 C13 1.341(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.403(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.389(6) . ?
C14 C19 1.414(6) . ?
C15 C16 1.344(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.351(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.411(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.420(6) . ?
C20 C21 1.468(6) . ?
C22 C27 1.362(6) . ?
C22 C23 1.367(6) . ?
C23 C24 1.372(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.356(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.380(6) . ?
C26 C27 1.362(6) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
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
C21 N1 C1 C2 -179.8(4) . . . . ?
C21 N1 C1 C6 -0.7(4) . . . . ?
N1 C1 C2 C3 -179.4(4) . . . . ?
C6 C1 C2 C3 1.7(6) . . . . ?
C1 C2 C3 C4 -0.7(7) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C5 C6 C1 1.0(7) . . . . ?
C4 C5 C6 C7 179.5(5) . . . . ?
N1 C1 C6 C5 179.0(4) . . . . ?
C2 C1 C6 C5 -1.8(6) . . . . ?
N1 C1 C6 C7 0.1(4) . . . . ?
C2 C1 C6 C7 179.2(4) . . . . ?
C5 C6 C7 C21 -178.1(5) . . . . ?
C1 C6 C7 C21 0.5(4) . . . . ?
C5 C6 C7 C8 7.2(8) . . . . ?
C1 C6 C7 C8 -174.2(4) . . . . ?
C21 C7 C8 C22 171.3(4) . . . . ?
C6 C7 C8 C22 -14.6(7) . . . . ?
C21 C7 C8 C9 -64.0(5) . . . . ?
C6 C7 C8 C9 110.1(5) . . . . ?
C7 C8 C9 C10 66.4(6) . . . . ?
C22 C8 C9 C10 -166.8(4) . . . . ?
C8 C9 C10 O1 169.6(4) . . . . ?
C8 C9 C10 C11 -8.4(7) . . . . ?
O1 C10 C11 C20 156.1(5) . . . . ?
C9 C10 C11 C20 -25.9(7) . . . . ?
O1 C10 C11 C12 -21.5(6) . . . . ?
C9 C10 C11 C12 156.4(5) . . . . ?
C20 C11 C12 C13 -2.5(7) . . . . ?
C10 C11 C12 C13 175.4(5) . . . . ?
C11 C12 C13 C14 4.8(7) . . . . ?
C12 C13 C14 C15 179.1(5) . . . . ?
C12 C13 C14 C19 0.7(7) . . . . ?
C13 C14 C15 C16 -176.3(5) . . . . ?
C19 C14 C15 C16 2.1(7) . . . . ?
C14 C15 C16 C17 4.3(8) . . . . ?
C15 C16 C17 C18 -6.4(8) . . . . ?
C16 C17 C18 C19 1.8(8) . . . . ?
C17 C18 C19 C14 4.5(7) . . . . ?
C17 C18 C19 C20 -175.2(5) . . . . ?
C15 C14 C19 C18 -6.4(7) . . . . ?
C13 C14 C19 C18 172.0(4) . . . . ?
C15 C14 C19 C20 173.3(4) . . . . ?
C13 C14 C19 C20 -8.3(6) . . . . ?
C12 C11 C20 C19 -5.2(6) . . . . ?
C10 C11 C20 C19 177.2(4) . . . . ?
C12 C11 C20 C21 169.2(4) . . . . ?
C10 C11 C20 C21 -8.4(7) . . . . ?
C18 C19 C20 C11 -169.8(4) . . . . ?
C14 C19 C20 C11 10.6(6) . . . . ?
C18 C19 C20 C21 15.6(6) . . . . ?
C14 C19 C20 C21 -164.1(4) . . . . ?
C1 N1 C21 C7 1.0(4) . . . . ?
C1 N1 C21 C20 178.2(4) . . . . ?
C6 C7 C21 N1 -1.0(4) . . . . ?
C8 C7 C21 N1 174.4(4) . . . . ?
C6 C7 C21 C20 -178.0(4) . . . . ?
C8 C7 C21 C20 -2.6(6) . . . . ?
C11 C20 C21 N1 -132.2(4) . . . . ?
C19 C20 C21 N1 42.2(5) . . . . ?
C11 C20 C21 C7 44.4(6) . . . . ?
C19 C20 C21 C7 -141.1(4) . . . . ?
C7 C8 C22 C27 -85.3(6) . . . . ?
C9 C8 C22 C27 150.2(5) . . . . ?
C7 C8 C22 C23 92.9(5) . . . . ?
C9 C8 C22 C23 -31.6(6) . . . . ?
C27 C22 C23 C24 -3.7(8) . . . . ?
C8 C22 C23 C24 178.0(4) . . . . ?
C22 C23 C24 C25 1.8(8) . . . . ?
C23 C24 C25 C26 0.9(7) . . . . ?
C23 C24 C25 Br1 -174.9(4) . . . . ?
C24 C25 C26 C27 -1.6(7) . . . . ?
Br1 C25 C26 C27 174.1(4) . . . . ?
C25 C26 C27 C22 -0.4(8) . . . . ?
C23 C22 C27 C26 3.0(8) . . . . ?
C8 C22 C27 C26 -178.7(4) . . . . ?
