#------------------------------------------------------------------------------
#$Date: 2024-09-06 02:14:58 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294429 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/34/7133414.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_7133414
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_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           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-17
_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            8
_cell_length_a                   15.1076(5)
_cell_length_b                   10.0376(5)
_cell_length_c                   20.6682(10)
_cell_measurement_reflns_used    3072
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4960
_cell_measurement_theta_min      3.8080
_cell_volume                     3134.2(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  86.00   1.00   12.50    --   18.74  19.00  30.00  103
  2  ω     45.00  83.00   1.00   12.50    --   18.74 178.00 -60.00   38
  3  ω    -47.00 -16.00   1.00   12.50    --  -18.85  77.00-180.00   31
  4  ω      8.00  33.00   1.00   12.50    --  -18.85  77.00-180.00   25
;
_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      0.0140502000
_diffrn_orient_matrix_UB_12      -0.0218395000
_diffrn_orient_matrix_UB_13      -0.0309670000
_diffrn_orient_matrix_UB_21      -0.0442929000
_diffrn_orient_matrix_UB_22      -0.0168731000
_diffrn_orient_matrix_UB_23      -0.0079161000
_diffrn_orient_matrix_UB_31      -0.0067470000
_diffrn_orient_matrix_UB_32      0.0650856000
_diffrn_orient_matrix_UB_33      -0.0124443000
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11690
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.094
_diffrn_reflns_theta_min         3.375
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96998
_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    1.540
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0391
_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)+(0.0301P)²+1.0344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2444
_reflns_number_total             3707
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02850c2.cif
_cod_data_source_block           20220117-zzx-lk-467-r
_cod_depositor_comments
'Adding full bibliography for 7133411--7133420.cif.'
_cod_database_code               7133414
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O Br'
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C13(H13), C1(H1), C16(H16), C17(H17), C14(H14), C4(H4),
 C2(H2), C3(H3)
;
_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 1.070
_oxdiff_exptl_absorpt_empirical_full_min 0.939
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'
'-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
Br1 Br 0.60912(2) 0.33335(3) 0.48450(2) 0.05109(12) Uani 1 1 d . . . . .
O1 O 0.86549(12) 0.25389(18) 0.62760(10) 0.0457(5) Uani 1 1 d . . . . .
C9 C 0.74532(15) 0.4246(2) 0.56961(13) 0.0308(6) Uani 1 1 d . . . . .
C11 C 0.77744(17) 0.4425(2) 0.45335(14) 0.0362(6) Uani 1 1 d . . . . .
C20 C 0.63060(17) 0.3495(2) 0.65620(13) 0.0331(6) Uani 1 1 d . . . . .
C21 C 0.71569(16) 0.3453(2) 0.62608(13) 0.0325(6) Uani 1 1 d . . . . .
C19 C 0.56391(17) 0.4394(3) 0.63615(14) 0.0379(6) Uani 1 1 d . . . . .
H19 H 0.575006 0.497448 0.602021 0.045 Uiso 1 1 calc R U . . .
C10 C 0.71718(17) 0.4185(2) 0.50871(14) 0.0341(6) Uani 1 1 d . . . . .
C5 C 0.85738(18) 0.3713(3) 0.45437(14) 0.0385(7) Uani 1 1 d . . . . .
C12 C 0.78059(18) 0.2629(3) 0.65121(13) 0.0365(6) Uani 1 1 d . . . . .
C6 C 0.87732(17) 0.2759(3) 0.50966(14) 0.0402(7) Uani 1 1 d . . . . .
H6A H 0.929791 0.224987 0.498726 0.048 Uiso 1 1 calc R U . . .
H6B H 0.828505 0.213703 0.513649 0.048 Uiso 1 1 calc R U . . .
C15 C 0.61255(19) 0.2648(3) 0.70979(14) 0.0378(6) Uani 1 1 d . . . . .
C8 C 0.83936(16) 0.4713(2) 0.58061(14) 0.0376(7) Uani 1 1 d . . . . .
H8A H 0.845893 0.511995 0.622912 0.045 Uiso 1 1 calc R U . . .
H8B H 0.857386 0.534647 0.547702 0.045 Uiso 1 1 calc R U . . .
C18 C 0.48342(18) 0.4422(3) 0.66629(15) 0.0451(7) Uani 1 1 d . . . . .
H18 H 0.440268 0.501586 0.652225 0.054 Uiso 1 1 calc R U . . .
C7 C 0.89225(17) 0.3435(3) 0.57585(15) 0.0408(7) Uani 1 1 d . . . . .
H7 H 0.955290 0.364223 0.580703 0.049 Uiso 1 1 calc R U . . .
C13 C 0.7627(2) 0.1804(3) 0.70520(14) 0.0440(7) Uani 1 1 d . . . . .
H13 H 0.806998 0.125966 0.721889 0.053 Uiso 1 1 calc R U . . .
C1 C 0.7577(2) 0.5277(3) 0.40242(15) 0.0469(7) Uani 1 1 d . . . . .
H1 H 0.704319 0.573872 0.401831 0.056 Uiso 1 1 calc R U . . .
C16 C 0.5279(2) 0.2708(3) 0.73930(15) 0.0492(8) Uani 1 1 d . . . . .
H16 H 0.515374 0.214653 0.773889 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4651(2) 0.3562(3) 0.71838(15) 0.0500(8) Uani 1 1 d . . . . .
H17 H 0.409883 0.358153 0.738295 0.060 Uiso 1 1 calc R U . . .
C14 C 0.6812(2) 0.1808(3) 0.73260(14) 0.0455(7) Uani 1 1 d . . . . .
H14 H 0.670052 0.124307 0.767321 0.055 Uiso 1 1 calc R U . . .
C4 C 0.9165(2) 0.3880(3) 0.40347(16) 0.0509(8) Uani 1 1 d . . . . .
H4 H 0.969680 0.341311 0.403326 0.061 Uiso 1 1 calc R U . . .
C2 C 0.8180(2) 0.5435(3) 0.35246(16) 0.0576(9) Uani 1 1 d . . . . .
H2 H 0.805473 0.601276 0.318476 0.069 Uiso 1 1 calc R U . . .
C3 C 0.8969(2) 0.4734(3) 0.35317(17) 0.0584(9) Uani 1 1 d . . . . .
H3 H 0.936983 0.483931 0.319424 0.070 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
C12 O1 C7 118.6(2) . . ?
C21 C9 C8 109.4(2) . . ?
C10 C9 C21 128.6(2) . . ?
C10 C9 C8 117.2(2) . . ?
C5 C11 C10 115.7(2) . . ?
C1 C11 C10 123.6(2) . . ?
C1 C11 C5 120.7(3) . . ?
C19 C20 C21 122.1(2) . . ?
C19 C20 C15 118.2(2) . . ?
C15 C20 C21 119.6(2) . . ?
C20 C21 C9 126.8(2) . . ?
C12 C21 C9 113.7(2) . . ?
C12 C21 C20 119.4(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 119.6 . . ?
C9 C10 Br1 122.8(2) . . ?
C9 C10 C11 121.8(2) . . ?
C11 C10 Br1 113.3(2) . . ?
C11 C5 C6 120.1(2) . . ?
C4 C5 C11 118.7(3) . . ?
C4 C5 C6 121.1(3) . . ?
O1 C12 C21 124.5(2) . . ?
O1 C12 C13 114.8(2) . . ?
C21 C12 C13 120.7(3) . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C5 C6 C7 114.7(2) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C16 C15 C20 118.8(3) . . ?
C14 C15 C20 118.3(3) . . ?
C14 C15 C16 122.8(3) . . ?
C9 C8 H8A 111.2 . . ?
C9 C8 H8B 111.2 . . ?
C9 C8 C7 102.88(19) . . ?
H8A C8 H8B 109.1 . . ?
C7 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
C19 C18 H18 119.6 . . ?
C19 C18 C17 120.8(3) . . ?
C17 C18 H18 119.6 . . ?
O1 C7 C6 109.8(2) . . ?
O1 C7 C8 109.2(2) . . ?
O1 C7 H7 109.0 . . ?
C6 C7 H7 109.0 . . ?
C8 C7 C6 110.6(2) . . ?
C8 C7 H7 109.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C11 C1 H1 120.2 . . ?
C2 C1 C11 119.6(3) . . ?
C2 C1 H1 120.2 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.1 . . ?
C15 C14 H14 119.1 . . ?
C13 C14 C15 121.8(3) . . ?
C13 C14 H14 119.1 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
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 C10 1.909(3) . ?
O1 C12 1.375(3) . ?
O1 C7 1.455(3) . ?
C9 C21 1.482(3) . ?
C9 C10 1.330(4) . ?
C9 C8 1.513(3) . ?
C11 C10 1.482(4) . ?
C11 C5 1.403(4) . ?
C11 C1 1.389(4) . ?
C20 C21 1.429(3) . ?
C20 C19 1.415(3) . ?
C20 C15 1.422(4) . ?
C21 C12 1.384(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.367(4) . ?
C5 C6 1.521(4) . ?
C5 C4 1.390(4) . ?
C12 C13 1.415(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.543(4) . ?
C15 C16 1.418(4) . ?
C15 C14 1.418(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.515(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.407(4) . ?
C7 H7 0.9800 . ?
C13 H13 0.9300 . ?
C13 C14 1.355(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.350(4) . ?
C17 H17 0.9300 . ?
C14 H14 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(4) . ?
C3 H3 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 C12 C13 C14 -179.9(2) . . . . ?
C9 C21 C12 O1 0.6(4) . . . . ?
C9 C21 C12 C13 -179.9(2) . . . . ?
C9 C8 C7 O1 -63.2(3) . . . . ?
C9 C8 C7 C6 57.9(3) . . . . ?
C11 C5 C6 C7 -68.0(3) . . . . ?
C11 C5 C4 C3 0.3(4) . . . . ?
C11 C1 C2 C3 0.8(5) . . . . ?
C20 C21 C12 O1 -177.8(2) . . . . ?
C20 C21 C12 C13 1.7(4) . . . . ?
C20 C19 C18 C17 0.5(4) . . . . ?
C20 C15 C16 C17 -1.1(4) . . . . ?
C20 C15 C14 C13 0.7(4) . . . . ?
C21 C9 C10 Br1 16.2(4) . . . . ?
C21 C9 C10 C11 -146.3(3) . . . . ?
C21 C9 C8 C7 69.7(3) . . . . ?
C21 C20 C19 C18 -179.3(2) . . . . ?
C21 C20 C15 C16 179.7(2) . . . . ?
C21 C20 C15 C14 1.5(4) . . . . ?
C21 C12 C13 C14 0.5(4) . . . . ?
C19 C20 C21 C9 -3.5(4) . . . . ?
C19 C20 C21 C12 174.7(2) . . . . ?
C19 C20 C15 C16 2.2(4) . . . . ?
C19 C20 C15 C14 -176.0(2) . . . . ?
C19 C18 C17 C16 0.7(4) . . . . ?
C10 C9 C21 C20 -66.7(4) . . . . ?
C10 C9 C21 C12 115.1(3) . . . . ?
C10 C9 C8 C7 -87.8(3) . . . . ?
C10 C11 C5 C6 0.5(4) . . . . ?
C10 C11 C5 C4 179.2(2) . . . . ?
C10 C11 C1 C2 -179.7(3) . . . . ?
C5 C11 C10 Br1 -114.3(2) . . . . ?
C5 C11 C10 C9 49.7(4) . . . . ?
C5 C11 C1 C2 -0.7(4) . . . . ?
C5 C6 C7 O1 150.6(2) . . . . ?
C5 C6 C7 C8 30.0(3) . . . . ?
C5 C4 C3 C2 -0.1(5) . . . . ?
C12 O1 C7 C6 -93.1(3) . . . . ?
C12 O1 C7 C8 28.4(3) . . . . ?
C12 C13 C14 C15 -1.7(4) . . . . ?
C6 C5 C4 C3 179.0(3) . . . . ?
C15 C20 C21 C9 179.1(2) . . . . ?
C15 C20 C21 C12 -2.7(4) . . . . ?
C15 C20 C19 C18 -1.9(4) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C8 C9 C21 C20 139.1(2) . . . . ?
C8 C9 C21 C12 -39.1(3) . . . . ?
C8 C9 C10 Br1 168.75(17) . . . . ?
C8 C9 C10 C11 6.3(4) . . . . ?
C7 O1 C12 C21 5.0(4) . . . . ?
C7 O1 C12 C13 -174.6(2) . . . . ?
C1 C11 C10 Br1 64.8(3) . . . . ?
C1 C11 C10 C9 -131.2(3) . . . . ?
C1 C11 C5 C6 -178.6(3) . . . . ?
C1 C11 C5 C4 0.2(4) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C16 C15 C14 C13 -177.4(3) . . . . ?
C14 C15 C16 C17 176.9(3) . . . . ?
C4 C5 C6 C7 113.3(3) . . . . ?
