#------------------------------------------------------------------------------
#$Date: 2019-11-04 10:38:41 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222508 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/39/4033932.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_4033932
loop_
_publ_author_name
'Gholap, Sachin P.'
'Jangid, Dashrath'
'Fernandes, Rodney A.'
_publ_section_title
;
 Metal-Free Brønsted Acid-Catalyzed Rearrangement of δ-Hydroxyalkynones
 to 2,3-Dihydro-4 H-pyran-4-ones: Total Synthesis of Obolactone and a
 Catechol Pyran Isolated from Plectranthus sylvestris.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3537
_journal_page_last               3551
_journal_paper_doi               10.1021/acs.joc.8b03141
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C11 H8 Br I O2'
_chemical_formula_sum            'C11 H8 Br I O2'
_chemical_formula_weight         378.98
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-14
_audit_creation_method
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.552(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7766(4)
_cell_length_b                   7.8221(3)
_cell_length_c                   13.4995(6)
_cell_measurement_reflns_used    4249
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.7520
_cell_measurement_theta_min      1.9180
_cell_volume                     1134.36(8)
_computing_cell_refinement
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    8.00    --  -20.00   0.00 -36.00  360
  2  ω    -70.00  -1.00   0.50    8.00    --  -20.00 -72.00-180.00  138
  3  ω    -59.00 -29.00   0.50    8.00    --  -20.00  72.00 -36.00   60
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0438388000
_diffrn_orient_matrix_UB_12      -0.0612409000
_diffrn_orient_matrix_UB_13      0.0140771000
_diffrn_orient_matrix_UB_21      0.0144834000
_diffrn_orient_matrix_UB_22      -0.0530339000
_diffrn_orient_matrix_UB_23      -0.0400738000
_diffrn_orient_matrix_UB_31      0.0472533000
_diffrn_orient_matrix_UB_32      -0.0407414000
_diffrn_orient_matrix_UB_33      0.0311565000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5777
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.896
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    6.321
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80984
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.219
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0292
_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)+(0.0235P)²+1.4297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0655
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1738
_reflns_number_total             1998
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b03141_si_005.cif
_cod_data_source_block           raf-spg-1265_mo
_cod_database_code               4033932
_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.
;
_reflns_odcompleteness_completeness 90.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.03
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C10(H10), C11(H11)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.853
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
I1 I 0.70145(3) 0.41276(4) 0.11758(2) 0.02462(12) Uani 1 1 d .
Br1 Br 0.83748(5) 0.09452(6) 0.38243(4) 0.03066(15) Uani 1 1 d .
O2 O 0.6247(3) 0.3998(4) 0.4258(2) 0.0212(7) Uani 1 1 d .
O1 O 0.4163(3) 0.3531(4) 0.1595(2) 0.0290(8) Uani 1 1 d .
C3 C 0.4185(4) 0.3915(6) 0.3366(4) 0.0240(11) Uani 1 1 d .
H3A H 0.3372 0.3319 0.3321 0.029 Uiso 1 1 calc R
H3B H 0.4039 0.5134 0.3517 0.029 Uiso 1 1 calc R
C5 C 0.6766(4) 0.4167(5) 0.3387(3) 0.0195(10) Uani 1 1 d .
C2 C 0.4764(4) 0.3769(5) 0.2393(4) 0.0204(10) Uani 1 1 d .
C9 C 1.0667(4) 0.5184(6) 0.3789(4) 0.0272(11) Uani 1 1 d .
H9 H 1.1534 0.5411 0.3879 0.033 Uiso 1 1 calc R
C8 C 1.0238(4) 0.3541(6) 0.3861(4) 0.0263(11) Uani 1 1 d .
H8 H 1.0807 0.2626 0.3992 0.032 Uiso 1 1 calc R
C1 C 0.6120(4) 0.4022(5) 0.2486(3) 0.0185(10) Uani 1 1 d .
C4 C 0.5043(4) 0.3127(6) 0.4191(3) 0.0231(10) Uani 1 1 d .
H4A H 0.4661 0.3229 0.4831 0.028 Uiso 1 1 calc R
H4B H 0.5162 0.1898 0.4053 0.028 Uiso 1 1 calc R
C6 C 0.8122(4) 0.4540(6) 0.3532(3) 0.0190(10) Uani 1 1 d .
C10 C 0.9833(4) 0.6517(6) 0.3584(3) 0.0246(11) Uani 1 1 d .
H10 H 1.0139 0.7649 0.3529 0.029 Uiso 1 1 calc R
C11 C 0.8562(4) 0.6224(6) 0.3459(3) 0.0234(11) Uani 1 1 d .
H11 H 0.7998 0.7144 0.3326 0.028 Uiso 1 1 calc R
C7 C 0.8972(4) 0.3222(5) 0.3742(3) 0.0202(10) Uani 1 1 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C5 O2 C4 114.7(3)
H3A C3 H3B 108.2
C2 C3 H3A 109.7
C2 C3 H3B 109.7
C2 C3 C4 109.8(4)
C4 C3 H3A 109.7
C4 C3 H3B 109.7
O2 C5 C1 123.7(4)
O2 C5 C6 112.0(4)
C1 C5 C6 124.3(4)
O1 C2 C3 123.6(4)
O1 C2 C1 123.1(5)
C1 C2 C3 113.2(4)
C8 C9 H9 120.0
C8 C9 C10 120.0(4)
C10 C9 H9 120.0
C9 C8 H8 120.2
C9 C8 C7 119.7(4)
C7 C8 H8 120.2
C5 C1 I1 121.2(3)
C5 C1 C2 121.5(4)
C2 C1 I1 117.2(3)
O2 C4 C3 110.0(4)
O2 C4 H4A 109.7
O2 C4 H4B 109.7
C3 C4 H4A 109.7
C3 C4 H4B 109.7
H4A C4 H4B 108.2
C11 C6 C5 120.5(4)
C7 C6 C5 120.3(4)
C7 C6 C11 119.2(4)
C9 C10 H10 119.4
C11 C10 C9 121.2(4)
C11 C10 H10 119.4
C6 C11 H11 120.6
C10 C11 C6 118.8(4)
C10 C11 H11 120.6
C8 C7 Br1 119.9(3)
C8 C7 C6 121.1(4)
C6 C7 Br1 119.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.082(5)
Br1 C7 1.900(4)
O2 C5 1.349(5)
O2 C4 1.462(5)
O1 C2 1.227(5)
C3 H3A 0.9900
C3 H3B 0.9900
C3 C2 1.502(6)
C3 C4 1.520(6)
C5 C1 1.357(6)
C5 C6 1.489(6)
C2 C1 1.470(6)
C9 H9 0.9500
C9 C8 1.372(6)
C9 C10 1.390(6)
C8 H8 0.9500
C8 C7 1.383(6)
C4 H4A 0.9900
C4 H4B 0.9900
C6 C11 1.406(6)
C6 C7 1.393(6)
C10 H10 0.9500
C10 C11 1.385(6)
C11 H11 0.9500
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
O2 C5 C1 I1 -175.5(3)
O2 C5 C1 C2 3.8(6)
O2 C5 C6 C11 -99.2(5)
O2 C5 C6 C7 80.8(5)
O1 C2 C1 I1 3.9(5)
O1 C2 C1 C5 -175.5(4)
C3 C2 C1 I1 -173.3(3)
C3 C2 C1 C5 7.3(6)
C5 O2 C4 C3 -49.7(5)
C5 C6 C11 C10 -179.1(4)
C5 C6 C7 Br1 0.8(6)
C5 C6 C7 C8 178.8(4)
C2 C3 C4 O2 59.1(5)
C9 C8 C7 Br1 179.2(4)
C9 C8 C7 C6 1.2(7)
C9 C10 C11 C6 -0.6(7)
C8 C9 C10 C11 0.6(7)
C1 C5 C6 C11 80.4(6)
C1 C5 C6 C7 -99.6(5)
C4 O2 C5 C1 18.5(6)
C4 O2 C5 C6 -161.9(3)
C4 C3 C2 O1 145.1(4)
C4 C3 C2 C1 -37.8(5)
C6 C5 C1 I1 4.8(6)
C6 C5 C1 C2 -175.8(4)
C10 C9 C8 C7 -0.9(7)
C11 C6 C7 Br1 -179.2(3)
C11 C6 C7 C8 -1.2(7)
C7 C6 C11 C10 0.9(7)
