#------------------------------------------------------------------------------
#$Date: 2024-09-06 01:14:58 +0200 (Fri 06 de Sep de 2024) $
#$Revision: 294429 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/34/7133418.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_7133418
loop_
_publ_author_name
'Li, Kai'
'Zhao, Zhengxing'
'Qin, Wenling'
'Liu, Yidong'
'Yan, Hailong'
_publ_section_title
;
 Catalytic asymmetric construction of bridged bicyclo[m.3.1] rings
 using an intramolecular Diels-Alder reaction.
;
_journal_issue                   71
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9570
_journal_page_last               9573
_journal_paper_doi               10.1039/d4cc02850c
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H15 Br O'
_chemical_formula_sum            'C21 H15 Br O'
_chemical_formula_weight         363.24
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-29
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-02-11 deposited with the CCDC.	2024-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8805(4)
_cell_length_b                   11.2373(4)
_cell_length_c                   17.8564(12)
_cell_measurement_reflns_used    1788
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3630
_cell_measurement_theta_min      3.8960
_cell_volume                     1581.28(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  45.00   1.00    4.00    --   18.74 -77.00  60.00   77
  2  ω      0.00  84.00   1.00    4.00    --   18.74  38.00-120.00   84
  3  ω    -74.00 -48.00   1.00    4.00    --  -18.85 178.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0823196000
_diffrn_orient_matrix_UB_12      -0.0233225000
_diffrn_orient_matrix_UB_13      0.0063979000
_diffrn_orient_matrix_UB_21      -0.0187517000
_diffrn_orient_matrix_UB_22      -0.0488271000
_diffrn_orient_matrix_UB_23      -0.0237788000
_diffrn_orient_matrix_UB_31      0.0310413000
_diffrn_orient_matrix_UB_32      0.0324160000
_diffrn_orient_matrix_UB_33      -0.0312326000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6083
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.096
_diffrn_reflns_theta_min         3.357
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 647 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0487
_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)+(0.0379P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.804
_reflns_number_gt                2126
_reflns_number_total             3598
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02850c2.cif
_cod_data_source_block           20211228-lk-467-up
_cod_depositor_comments
'Adding full bibliography for 7133411--7133420.cif.'
_cod_database_code               7133418
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H Br O'
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C14(H14), C17(H17), C16(H16), C20(H20), C19(H19), C7(H7),
 C15(H15), C8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.239
_oxdiff_exptl_absorpt_empirical_full_min 0.800
loop_
_space_group_symop_operation_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_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
Br2 Br 0.73281(9) 0.65207(5) 0.68054(4) 0.0765(3) Uani 1 1 d . . . . .
O1 O 0.8174(4) 0.1118(3) 0.7522(2) 0.0530(11) Uani 1 1 d . . . . .
C2 C 0.6502(7) 0.4032(4) 0.6953(3) 0.0426(14) Uani 1 1 d . . . . .
H2 H 0.575878 0.414705 0.651903 0.051 Uiso 1 1 calc R U . . .
C3 C 0.5480(7) 0.4224(5) 0.7666(3) 0.0502(15) Uani 1 1 d . . . . .
H3A H 0.522905 0.506590 0.771415 0.060 Uiso 1 1 calc R U . . .
H3B H 0.440789 0.380616 0.761928 0.060 Uiso 1 1 calc R U . . .
C4 C 0.6352(7) 0.3812(4) 0.8366(3) 0.0451(15) Uani 1 1 d . . . . .
C12 C 0.7554(7) 0.1915(4) 0.6377(3) 0.0427(13) Uani 1 1 d . . . . .
C11 C 0.7157(6) 0.2769(4) 0.6951(3) 0.0405(14) Uani 1 1 d . . . . .
C13 C 0.7443(6) 0.1867(4) 0.5578(3) 0.0441(13) Uani 1 1 d . . . . .
C10 C 0.7557(7) 0.2258(4) 0.7611(3) 0.0434(12) Uani 1 1 d . . . . .
C1 C 0.8016(6) 0.4870(4) 0.6888(3) 0.0473(14) Uani 1 1 d . . . . .
H1A H 0.867888 0.465492 0.645123 0.057 Uiso 1 1 calc R U . . .
H1B H 0.873331 0.477705 0.732579 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7374(7) 0.2785(4) 0.8346(3) 0.0464(13) Uani 1 1 d . . . . .
C18 C 0.7919(6) 0.0783(5) 0.5223(4) 0.0502(15) Uani 1 1 d . . . . .
C6 C 0.6875(8) 0.3932(6) 0.9694(4) 0.0611(17) Uani 1 1 d . . . . .
H6 H 0.670165 0.431770 1.014820 0.073 Uiso 1 1 calc R U . . .
C5 C 0.6116(8) 0.4377(5) 0.9047(4) 0.0562(17) Uani 1 1 d . . . . .
H5 H 0.544697 0.505710 0.907352 0.067 Uiso 1 1 calc R U . . .
C21 C 0.8153(6) 0.0927(5) 0.6757(4) 0.0475(14) Uani 1 1 d . . . . .
C14 C 0.6922(7) 0.2810(5) 0.5128(3) 0.0530(16) Uani 1 1 d . . . . .
H14 H 0.662426 0.352686 0.535324 0.064 Uiso 1 1 calc R U . . .
C17 C 0.7804(7) 0.0711(5) 0.4432(4) 0.0604(18) Uani 1 1 d . . . . .
H17 H 0.809617 0.000496 0.419249 0.072 Uiso 1 1 calc R U . . .
C16 C 0.7279(7) 0.1646(6) 0.4020(4) 0.0686(17) Uani 1 1 d . . . . .
H16 H 0.721310 0.157934 0.350169 0.082 Uiso 1 1 calc R U . . .
C20 C 0.8651(7) -0.0147(5) 0.6419(4) 0.0558(18) Uani 1 1 d . . . . .
H20 H 0.904482 -0.079004 0.669757 0.067 Uiso 1 1 calc R U . . .
C19 C 0.8524(7) -0.0190(5) 0.5668(4) 0.0600(19) Uani 1 1 d . . . . .
H19 H 0.884456 -0.088665 0.542476 0.072 Uiso 1 1 calc R U . . .
C7 C 0.7876(8) 0.2932(5) 0.9669(4) 0.0621(17) Uani 1 1 d . . . . .
H7 H 0.837491 0.264158 1.010422 0.075 Uiso 1 1 calc R U . . .
C15 C 0.6834(7) 0.2714(6) 0.4367(4) 0.0612(18) Uani 1 1 d . . . . .
H15 H 0.647851 0.335931 0.408111 0.073 Uiso 1 1 calc R U . . .
C8 C 0.8139(7) 0.2356(5) 0.8989(4) 0.0544(16) Uani 1 1 d . . . . .
H8 H 0.882727 0.168480 0.896640 0.065 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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
C10 O1 C21 104.7(4) . . ?
C3 C2 H2 109.0 . . ?
C3 C2 C1 113.0(5) . . ?
C11 C2 H2 109.0 . . ?
C11 C2 C3 108.4(4) . . ?
C11 C2 C1 108.3(4) . . ?
C1 C2 H2 109.0 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.2(5) . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C9 C4 C3 119.6(5) . . ?
C5 C4 C3 121.9(5) . . ?
C5 C4 C9 118.4(5) . . ?
C13 C12 C11 136.3(5) . . ?
C21 C12 C11 105.0(5) . . ?
C21 C12 C13 118.7(5) . . ?
C12 C11 C2 134.6(5) . . ?
C10 C11 C2 118.5(5) . . ?
C10 C11 C12 106.8(4) . . ?
C18 C13 C12 117.4(5) . . ?
C14 C13 C12 124.4(5) . . ?
C14 C13 C18 118.2(5) . . ?
O1 C10 C9 121.3(5) . . ?
C11 C10 O1 112.1(4) . . ?
C11 C10 C9 126.5(4) . . ?
Br2 C1 H1A 109.2 . . ?
Br2 C1 H1B 109.2 . . ?
C2 C1 Br2 112.2(3) . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C4 C9 C10 114.6(5) . . ?
C8 C9 C4 120.9(5) . . ?
C8 C9 C10 124.5(5) . . ?
C13 C18 C19 119.5(6) . . ?
C17 C18 C13 118.4(5) . . ?
C17 C18 C19 122.0(6) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.9(6) . . ?
C4 C5 C6 120.4(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
O1 C21 C12 111.4(4) . . ?
O1 C21 C20 123.7(5) . . ?
C12 C21 C20 124.9(6) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.0(6) . . ?
C15 C14 H14 119.0 . . ?
C18 C17 H17 119.4 . . ?
C16 C17 C18 121.2(5) . . ?
C16 C17 H17 119.4 . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C15 120.3(6) . . ?
C15 C16 H16 119.8 . . ?
C21 C20 H20 122.0 . . ?
C19 C20 C21 116.0(6) . . ?
C19 C20 H20 122.0 . . ?
C18 C19 H19 118.3 . . ?
C20 C19 C18 123.4(6) . . ?
C20 C19 H19 118.3 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(6) . . ?
C8 C7 H7 120.2 . . ?
C14 C15 C16 119.8(6) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C9 C8 C7 119.8(6) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
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
Br2 C1 1.938(4) . ?
O1 C10 1.379(5) . ?
O1 C21 1.381(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.522(7) . ?
C2 C11 1.511(6) . ?
C2 C1 1.525(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.500(7) . ?
C4 C9 1.408(7) . ?
C4 C5 1.385(7) . ?
C12 C11 1.438(7) . ?
C12 C13 1.430(7) . ?
C12 C21 1.385(7) . ?
C11 C10 1.348(6) . ?
C13 C18 1.424(7) . ?
C13 C14 1.391(7) . ?
C10 C9 1.447(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C9 C8 1.383(7) . ?
C18 C17 1.417(8) . ?
C18 C19 1.433(8) . ?
C6 H6 0.9300 . ?
C6 C5 1.392(8) . ?
C6 C7 1.374(8) . ?
C5 H5 0.9300 . ?
C21 C20 1.406(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.365(8) . ?
C17 H17 0.9300 . ?
C17 C16 1.347(8) . ?
C16 H16 0.9300 . ?
C16 C15 1.396(8) . ?
C20 H20 0.9300 . ?
C20 C19 1.347(8) . ?
C19 H19 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.392(8) . ?
C15 H15 0.9300 . ?
C8 H8 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
O1 C10 C9 C4 -164.8(4) . . . . ?
O1 C10 C9 C8 16.2(8) . . . . ?
O1 C21 C20 C19 178.9(5) . . . . ?
C2 C3 C4 C9 -35.7(7) . . . . ?
C2 C3 C4 C5 147.6(5) . . . . ?
C2 C11 C10 O1 -178.6(4) . . . . ?
C2 C11 C10 C9 2.2(8) . . . . ?
C3 C2 C11 C12 149.8(6) . . . . ?
C3 C2 C11 C10 -33.1(6) . . . . ?
C3 C2 C1 Br2 -64.5(5) . . . . ?
C3 C4 C9 C10 3.6(7) . . . . ?
C3 C4 C9 C8 -177.4(5) . . . . ?
C3 C4 C5 C6 176.6(5) . . . . ?
C4 C9 C8 C7 1.1(8) . . . . ?
C12 C11 C10 O1 -0.7(6) . . . . ?
C12 C11 C10 C9 180.0(5) . . . . ?
C12 C13 C18 C17 179.4(5) . . . . ?
C12 C13 C18 C19 -1.6(7) . . . . ?
C12 C13 C14 C15 -179.8(5) . . . . ?
C12 C21 C20 C19 0.1(8) . . . . ?
C11 C2 C3 C4 48.3(6) . . . . ?
C11 C2 C1 Br2 175.4(4) . . . . ?
C11 C12 C13 C18 -177.0(6) . . . . ?
C11 C12 C13 C14 3.8(10) . . . . ?
C11 C12 C21 O1 -0.8(6) . . . . ?
C11 C12 C21 C20 178.1(5) . . . . ?
C11 C10 C9 C4 14.4(8) . . . . ?
C11 C10 C9 C8 -164.6(5) . . . . ?
C13 C12 C11 C2 -3.1(11) . . . . ?
C13 C12 C11 C10 179.6(6) . . . . ?
C13 C12 C21 O1 -179.8(4) . . . . ?
C13 C12 C21 C20 -0.9(8) . . . . ?
C13 C18 C17 C16 0.9(9) . . . . ?
C13 C18 C19 C20 0.9(8) . . . . ?
C13 C14 C15 C16 -0.1(9) . . . . ?
C10 O1 C21 C12 0.4(6) . . . . ?
C10 O1 C21 C20 -178.5(5) . . . . ?
C10 C9 C8 C7 -179.9(5) . . . . ?
C1 C2 C3 C4 -71.6(6) . . . . ?
C1 C2 C11 C12 -87.3(7) . . . . ?
C1 C2 C11 C10 89.8(6) . . . . ?
C9 C4 C5 C6 -0.1(8) . . . . ?
C18 C13 C14 C15 1.0(8) . . . . ?
C18 C17 C16 C15 0.0(9) . . . . ?
C6 C7 C8 C9 -0.9(8) . . . . ?
C5 C4 C9 C10 -179.7(5) . . . . ?
C5 C4 C9 C8 -0.6(7) . . . . ?
C5 C6 C7 C8 0.1(8) . . . . ?
C21 O1 C10 C11 0.2(6) . . . . ?
C21 O1 C10 C9 179.6(5) . . . . ?
C21 C12 C11 C2 178.2(5) . . . . ?
C21 C12 C11 C10 0.9(6) . . . . ?
C21 C12 C13 C18 1.6(7) . . . . ?
C21 C12 C13 C14 -177.6(5) . . . . ?
C21 C20 C19 C18 -0.1(8) . . . . ?
C14 C13 C18 C17 -1.4(7) . . . . ?
C14 C13 C18 C19 177.6(5) . . . . ?
C17 C18 C19 C20 179.9(6) . . . . ?
C17 C16 C15 C14 -0.4(9) . . . . ?
C19 C18 C17 C16 -178.1(5) . . . . ?
C7 C6 C5 C4 0.3(8) . . . . ?
