#------------------------------------------------------------------------------
#$Date: 2019-11-23 19:47:02 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234714 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/64/4036454.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_4036454
loop_
_publ_author_name
'Hooper, Joel F.'
'James, Natalie C.'
'Bozkurt, Esra'
'Aviyente, Viktorya'
'White, Jonathan M.'
'Holland, Mareike C.'
'Gilmour, Ryan'
'Holmes, Andrew B.'
'Houk, K. N.'
_publ_section_title
;
 Medium-Ring Effects on the Endo/Exo Selectivity of the Organocatalytic
 Intramolecular Diels-Alder Reaction.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12058
_journal_page_last               12075
_journal_paper_doi               10.1021/acs.joc.5b02037
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C10 H14 Br2 O3'
_chemical_formula_weight         342.03
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 111.066(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1597(12)
_cell_length_b                   24.878(5)
_cell_length_c                   7.5576(15)
_cell_measurement_reflns_used    1907
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      27.22
_cell_measurement_theta_min      3.28
_cell_volume                     1080.7(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130.0(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5580
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.637
_exptl_absorpt_coefficient_mu    7.484
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.102
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0300
_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)+(0.0402P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0726
_refine_ls_wR_factor_ref         0.0747
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1655
_reflns_number_total             1899
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo5b02037_si_002.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4036454
_shelx_shelxl_version_number     2014/7
_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.
;
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
H H 0.688(5) 0.7867(16) 0.866(7) 0.057(18) Uiso 1 1 d D .
Br1 Br 0.40785(7) 0.53150(2) 0.66154(5) 0.01796(14) Uani 1 1 d . .
Br2 Br 0.26806(7) 0.61191(2) 1.15489(5) 0.02410(15) Uani 1 1 d . .
O3 O -0.0563(4) 0.66897(9) 0.4122(3) 0.0167(6) Uani 1 1 d . .
O1 O 0.8046(5) 0.70550(11) 0.8099(4) 0.0271(7) Uani 1 1 d . .
C10 C 0.0580(7) 0.53128(14) 0.8111(6) 0.0199(9) Uani 1 1 d . .
H10A H -0.0483 0.5490 0.8628 0.030 Uiso 1 1 calc R U
H10B H 0.1391 0.5019 0.8956 0.030 Uiso 1 1 calc R U
H10C H -0.0307 0.5168 0.6853 0.030 Uiso 1 1 calc R U
C7 C 0.6335(6) 0.71803(15) 0.8378(5) 0.0165(8) Uani 1 1 d . .
C1 C 0.4585(6) 0.67842(14) 0.8553(5) 0.0147(8) Uani 1 1 d . .
H1 H 0.3652 0.6957 0.9240 0.018 Uiso 1 1 calc R U
C9 C -0.0519(7) 0.61661(14) 0.4907(5) 0.0169(8) Uani 1 1 d . .
H9A H -0.0049 0.5893 0.4162 0.020 Uiso 1 1 calc R U
H9B H -0.2067 0.6069 0.4931 0.020 Uiso 1 1 calc R U
C3 C 0.1235(6) 0.62054(13) 0.6870(5) 0.0134(8) Uani 1 1 d . .
H3 H 0.0444 0.6393 0.7641 0.016 Uiso 1 1 calc R U
C2 C 0.2970(6) 0.65998(14) 0.6632(5) 0.0134(8) Uani 1 1 d . .
H2 H 0.3900 0.6419 0.5959 0.016 Uiso 1 1 calc R U
C4 C 0.2316(6) 0.57103(14) 0.7956(5) 0.0132(8) Uani 1 1 d . .
C6 C 0.5814(6) 0.62957(15) 0.9654(5) 0.0168(8) Uani 1 1 d . .
H6A H 0.6834 0.6142 0.9026 0.020 Uiso 1 1 calc R U
H6B H 0.6816 0.6410 1.0945 0.020 Uiso 1 1 calc R U
C8 C 0.1373(6) 0.69999(15) 0.5330(5) 0.0184(8) Uani 1 1 d . .
H8A H 0.0851 0.7269 0.6055 0.022 Uiso 1 1 calc R U
H8B H 0.2159 0.7189 0.4573 0.022 Uiso 1 1 calc R U
C5 C 0.4185(7) 0.58683(15) 0.9811(5) 0.0160(8) Uani 1 1 d . .
H5 H 0.5120 0.5541 1.0374 0.019 Uiso 1 1 calc R U
O2 O 0.5762(5) 0.76744(10) 0.8572(4) 0.0239(7) Uani 1 1 d D .
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'
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
C8 O3 C9 109.8(3)
C4 C10 H10A 109.5
C4 C10 H10B 109.5
H10A C10 H10B 109.5
C4 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O1 C7 O2 124.2(4)
O1 C7 C1 123.7(3)
O2 C7 C1 112.2(3)
C7 C1 C2 111.2(3)
C7 C1 C6 110.0(3)
C2 C1 C6 108.2(3)
C7 C1 H1 109.1
C2 C1 H1 109.1
C6 C1 H1 109.1
O3 C9 C3 104.6(3)
O3 C9 H9A 110.8
C3 C9 H9A 110.8
O3 C9 H9B 110.8
C3 C9 H9B 110.8
H9A C9 H9B 108.9
C4 C3 C9 120.8(3)
C4 C3 C2 113.9(3)
C9 C3 C2 102.4(3)
C4 C3 H3 106.2
C9 C3 H3 106.2
C2 C3 H3 106.2
C8 C2 C1 118.9(3)
C8 C2 C3 100.7(3)
C1 C2 C3 109.5(3)
C8 C2 H2 109.1
C1 C2 H2 109.1
C3 C2 H2 109.1
C10 C4 C3 113.5(3)
C10 C4 C5 115.3(3)
C3 C4 C5 109.6(3)
C10 C4 Br1 104.5(2)
C3 C4 Br1 110.1(2)
C5 C4 Br1 103.2(2)
C5 C6 C1 113.4(3)
C5 C6 H6A 108.9
C1 C6 H6A 108.9
C5 C6 H6B 108.9
C1 C6 H6B 108.9
H6A C6 H6B 107.7
O3 C8 C2 105.1(3)
O3 C8 H8A 110.7
C2 C8 H8A 110.7
O3 C8 H8B 110.7
C2 C8 H8B 110.7
H8A C8 H8B 108.8
C6 C5 C4 114.8(3)
C6 C5 Br2 108.6(2)
C4 C5 Br2 108.5(2)
C6 C5 H5 108.2
C4 C5 H5 108.2
Br2 C5 H5 108.2
C7 O2 H 108(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.991(3)
Br2 C5 1.962(3)
O3 C8 1.438(4)
O3 C9 1.428(4)
O1 C7 1.188(4)
C10 C4 1.492(5)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C7 O2 1.302(4)
C7 C1 1.501(5)
C1 C2 1.506(5)
C1 C6 1.513(5)
C1 H1 1.0000
C9 C3 1.492(5)
C9 H9A 0.9900
C9 H9B 0.9900
C3 C4 1.497(5)
C3 C2 1.509(5)
C3 H3 1.0000
C2 C8 1.494(5)
C2 H2 1.0000
C4 C5 1.512(5)
C6 C5 1.495(5)
C6 H6A 0.9900
C6 H6B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C5 H5 1.0000
O2 H 0.819(5)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10C Br1 0.98 3.05 4.008(4) 164.7 3_566
C9 H9A Br2 0.99 3.07 3.733(4) 125.4 1_554
C3 H3 O1 1.00 2.32 3.241(4) 152.8 1_455
C2 H2 Br1 1.00 2.78 3.270(4) 110.3 .
C6 H6B O3 0.99 2.46 3.453(4) 177.9 1_656
C8 H8B O2 0.99 2.61 3.508(5) 150.6 4_575
C5 H5 Br1 1.00 3.02 3.877(4) 143.8 3_667
