#------------------------------------------------------------------------------
#$Date: 2024-12-06 17:15:29 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296288 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/36/7133657.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_7133657
loop_
_publ_author_name
'Kumar, Manoj'
'Singh, Shubham'
'Subramanian, Parthasarathi'
_publ_section_title
;
 Synthesis of dispiro-orthoester via an acetal oxo-carbenium ion.
;
_journal_issue                   88
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12860
_journal_page_last               12863
_journal_paper_doi               10.1039/d4cc03031a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         '0.133(C14 H16 Br2 O4)'
_chemical_formula_sum            'C1.87 H2.13 Br0.27 O0.53'
_chemical_formula_weight         54.41
_chemical_name_systematic
3,3-bis(bromomethyl)-1,5,7-trioxadispiro[5.1.58.26]pentadeca-9,12-dien-11-one
_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     dual
_audit_creation_date             2024-02-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-02-05 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.2440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            30
_cell_length_a                   11.1660(3)
_cell_length_b                   10.3032(3)
_cell_length_c                   13.0230(3)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.53
_cell_volume                     1489.35(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD 6000'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24644
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.376
_diffrn_reflns_theta_min         2.526
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.452
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5224
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0805 before and 0.0439 after correction.
The Ratio of minimum to maximum transmission is 0.7005.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_preparation       acetone
_exptl_crystal_recrystallization_method 'slow evaporation'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0194
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0151P)²+1.2115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0434
_refine_ls_wR_factor_ref         0.0443
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3421
_reflns_number_total             3720
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc03031a2.cif
_cod_data_source_block           15sepa_o_0m
_cod_depositor_comments
'Adding full bibliography for 7133655--7133659.cif.'
_cod_database_code               7133657
_shelx_shelxl_version_number     2019/3
_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.a Secondary CH2 refined with riding coordinates:
 C007(H00A,H00B), C00A(H00C,H00D), C00B(H00E,H00F), C00E(H00H,H00I), C00F(H00J,
 H00K), C00G(H00L,H00M)
1.b Aromatic/amide H refined with riding coordinates:
 C00D(H00G), C00H(H00N), C00J(H00O), C00K(H00P)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 0.89283(2) 0.13467(2) 0.60936(2) 0.01618(5) Uani 1 1 d . . . . .
Br02 Br 0.88398(2) 0.39428(2) 0.82851(2) 0.01922(5) Uani 1 1 d . . . . .
O003 O 0.85517(10) 0.55578(10) 0.47911(8) 0.0136(2) Uani 1 1 d . . . . .
O004 O 0.71881(10) 0.61890(10) 0.59170(8) 0.0143(2) Uani 1 1 d . . . . .
O005 O 0.65450(10) 0.59729(11) 0.42011(8) 0.0145(2) Uani 1 1 d . . . . .
O006 O 0.45872(12) 0.66307(14) 0.03965(10) 0.0294(3) Uani 1 1 d . . . . .
C007 C 0.90781(14) 0.43893(15) 0.68576(12) 0.0147(3) Uani 1 1 d . . . . .
H00A H 0.919893 0.531893 0.681139 0.018 Uiso 1 1 calc R U . . .
H00B H 0.980272 0.396506 0.667875 0.018 Uiso 1 1 calc R U . . .
C008 C 0.80205(14) 0.39941(14) 0.60763(12) 0.0120(3) Uani 1 1 d . . . . .
C009 C 0.75343(14) 0.63258(14) 0.49283(12) 0.0125(3) Uani 1 1 d . . . . .
C00A C 0.76868(14) 0.76555(15) 0.34900(12) 0.0151(3) Uani 1 1 d . . . . .
H00C H 0.840773 0.732985 0.322425 0.018 Uiso 1 1 calc R U . . .
H00D H 0.749629 0.850608 0.319730 0.018 Uiso 1 1 calc R U . . .
C00B C 0.83808(14) 0.42032(15) 0.49854(12) 0.0137(3) Uani 1 1 d . . . . .
H00E H 0.912094 0.373621 0.491199 0.016 Uiso 1 1 calc R U . . .
H00F H 0.775658 0.386092 0.448175 0.016 Uiso 1 1 calc R U . . .
C00C C 0.66126(14) 0.67004(15) 0.32509(12) 0.0132(3) Uani 1 1 d . . . . .
C00D C 0.68304(14) 0.57543(15) 0.24172(12) 0.0151(3) Uani 1 1 d . . . . .
H00G H 0.746760 0.517404 0.254211 0.018 Uiso 1 1 calc R U . . .
C00E C 0.69166(14) 0.48651(15) 0.61670(12) 0.0136(3) Uani 1 1 d . . . . .
H00H H 0.624072 0.455716 0.569948 0.016 Uiso 1 1 calc R U . . .
H00I H 0.669260 0.482287 0.686529 0.016 Uiso 1 1 calc R U . . .
C00F C 0.78439(15) 0.77050(15) 0.46686(12) 0.0156(3) Uani 1 1 d . . . . .
H00J H 0.866448 0.792254 0.493486 0.019 Uiso 1 1 calc R U . . .
H00K H 0.729460 0.832080 0.493080 0.019 Uiso 1 1 calc R U . . .
C00G C 0.76208(14) 0.25975(15) 0.61944(12) 0.0142(3) Uani 1 1 d . . . . .
H00L H 0.696735 0.240645 0.566263 0.017 Uiso 1 1 calc R U . . .
H00M H 0.731560 0.249771 0.685943 0.017 Uiso 1 1 calc R U . . .
C00H C 0.61614(15) 0.56995(16) 0.15075(12) 0.0166(3) Uani 1 1 d . . . . .
H00N H 0.633406 0.508236 0.102368 0.020 Uiso 1 1 calc R U . . .
C00I C 0.51487(15) 0.66070(17) 0.12583(13) 0.0182(3) Uani 1 1 d . . . . .
C00J C 0.48327(15) 0.74612(17) 0.20947(13) 0.0181(3) Uani 1 1 d . . . . .
H00O H 0.417274 0.801216 0.197376 0.022 Uiso 1 1 calc R U . . .
C00K C 0.54707(14) 0.74623(16) 0.30201(12) 0.0159(3) Uani 1 1 d . . . . .
H00P H 0.519686 0.795605 0.354494 0.019 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
C009 O003 C00B 113.49(12) . . ?
C009 O004 C00E 113.02(11) . . ?
C009 O005 C00C 109.04(11) . . ?
Br02 C007 H00A 108.9 . . ?
Br02 C007 H00B 108.9 . . ?
H00A C007 H00B 107.8 . . ?
C008 C007 Br02 113.20(10) . . ?
C008 C007 H00A 108.9 . . ?
C008 C007 H00B 108.9 . . ?
C007 C008 C00B 108.54(12) . . ?
C007 C008 C00E 111.16(13) . . ?
C00B C008 C00E 106.39(12) . . ?
C00G C008 C007 113.54(13) . . ?
C00G C008 C00B 109.66(12) . . ?
C00G C008 C00E 107.33(12) . . ?
O003 C009 O005 110.48(12) . . ?
O003 C009 C00F 106.99(12) . . ?
O004 C009 O003 111.64(12) . . ?
O004 C009 O005 108.46(12) . . ?
O004 C009 C00F 113.34(12) . . ?
O005 C009 C00F 105.77(12) . . ?
H00C C00A H00D 109.1 . . ?
C00C C00A H00C 111.2 . . ?
C00C C00A H00D 111.2 . . ?
C00F C00A H00C 111.2 . . ?
C00F C00A H00D 111.2 . . ?
C00F C00A C00C 102.94(12) . . ?
O003 C00B C008 110.70(12) . . ?
O003 C00B H00E 109.5 . . ?
O003 C00B H00F 109.5 . . ?
C008 C00B H00E 109.5 . . ?
C008 C00B H00F 109.5 . . ?
H00E C00B H00F 108.1 . . ?
O005 C00C C00A 105.40(12) . . ?
O005 C00C C00D 107.97(12) . . ?
O005 C00C C00K 108.56(12) . . ?
C00D C00C C00A 111.96(13) . . ?
C00D C00C C00K 113.38(13) . . ?
C00K C00C C00A 109.21(13) . . ?
C00C C00D H00G 118.2 . . ?
C00H C00D C00C 123.56(15) . . ?
C00H C00D H00G 118.2 . . ?
O004 C00E C008 110.14(12) . . ?
O004 C00E H00H 109.6 . . ?
O004 C00E H00I 109.6 . . ?
C008 C00E H00H 109.6 . . ?
C008 C00E H00I 109.6 . . ?
H00H C00E H00I 108.1 . . ?
C009 C00F C00A 100.94(12) . . ?
C009 C00F H00J 111.6 . . ?
C009 C00F H00K 111.6 . . ?
C00A C00F H00J 111.6 . . ?
C00A C00F H00K 111.6 . . ?
H00J C00F H00K 109.4 . . ?
Br01 C00G H00L 109.0 . . ?
Br01 C00G H00M 109.0 . . ?
C008 C00G Br01 112.73(10) . . ?
C008 C00G H00L 109.0 . . ?
C008 C00G H00M 109.0 . . ?
H00L C00G H00M 107.8 . . ?
C00D C00H H00N 119.6 . . ?
C00D C00H C00I 120.74(15) . . ?
C00I C00H H00N 119.6 . . ?
O006 C00I C00H 121.18(16) . . ?
O006 C00I C00J 121.72(16) . . ?
C00J C00I C00H 117.09(14) . . ?
C00I C00J H00O 119.3 . . ?
C00K C00J C00I 121.48(15) . . ?
C00K C00J H00O 119.3 . . ?
C00C C00K H00P 118.6 . . ?
C00J C00K C00C 122.71(15) . . ?
C00J C00K H00P 118.6 . . ?
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
Br01 C00G 1.9623(15) . ?
Br02 C007 1.9612(15) . ?
O003 C009 1.4117(18) . ?
O003 C00B 1.4349(18) . ?
O004 C009 1.3912(18) . ?
O004 C00E 1.4422(18) . ?
O005 C009 1.4219(18) . ?
O005 C00C 1.4557(18) . ?
O006 C00I 1.225(2) . ?
C007 H00A 0.9700 . ?
C007 H00B 0.9700 . ?
C007 C008 1.528(2) . ?
C008 C00B 1.533(2) . ?
C008 C00E 1.540(2) . ?
C008 C00G 1.519(2) . ?
C009 C00F 1.510(2) . ?
C00A H00C 0.9700 . ?
C00A H00D 0.9700 . ?
C00A C00C 1.557(2) . ?
C00A C00F 1.527(2) . ?
C00B H00E 0.9700 . ?
C00B H00F 0.9700 . ?
C00C C00D 1.498(2) . ?
C00C C00K 1.500(2) . ?
C00D H00G 0.9300 . ?
C00D C00H 1.331(2) . ?
C00E H00H 0.9700 . ?
C00E H00I 0.9700 . ?
C00F H00J 0.9700 . ?
C00F H00K 0.9700 . ?
C00G H00L 0.9700 . ?
C00G H00M 0.9700 . ?
C00H H00N 0.9300 . ?
C00H C00I 1.476(2) . ?
C00I C00J 1.473(2) . ?
C00J H00O 0.9300 . ?
C00J C00K 1.332(2) . ?
C00K H00P 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
Br02 C007 C008 C00B -171.72(10) . . . . ?
Br02 C007 C008 C00E 71.61(14) . . . . ?
Br02 C007 C008 C00G -49.52(16) . . . . ?
O003 C009 C00F C00A 77.99(14) . . . . ?
O004 C009 C00F C00A -158.52(13) . . . . ?
O005 C009 C00F C00A -39.82(15) . . . . ?
O005 C00C C00D C00H 128.01(16) . . . . ?
O005 C00C C00K C00J -131.14(16) . . . . ?
O006 C00I C00J C00K -177.74(17) . . . . ?
C007 C008 C00B O003 -65.90(16) . . . . ?
C007 C008 C00E O004 63.38(16) . . . . ?
C007 C008 C00G Br01 -56.93(15) . . . . ?
C009 O003 C00B C008 -56.36(16) . . . . ?
C009 O004 C00E C008 58.46(16) . . . . ?
C009 O005 C00C C00A -5.32(15) . . . . ?
C009 O005 C00C C00D 114.49(13) . . . . ?
C009 O005 C00C C00K -122.22(13) . . . . ?
C00A C00C C00D C00H -116.41(17) . . . . ?
C00A C00C C00K C00J 114.43(17) . . . . ?
C00B O003 C009 O004 56.99(16) . . . . ?
C00B O003 C009 O005 -63.80(15) . . . . ?
C00B O003 C009 C00F -178.48(12) . . . . ?
C00B C008 C00E O004 -54.59(15) . . . . ?
C00B C008 C00G Br01 64.66(14) . . . . ?
C00C O005 C009 O003 -86.76(14) . . . . ?
C00C O005 C009 O004 150.57(12) . . . . ?
C00C O005 C009 C00F 28.68(15) . . . . ?
C00C C00A C00F C009 35.07(15) . . . . ?
C00C C00D C00H C00I 0.9(2) . . . . ?
C00D C00C C00K C00J -11.2(2) . . . . ?
C00D C00H C00I O006 174.31(17) . . . . ?
C00D C00H C00I C00J -6.8(2) . . . . ?
C00E O004 C009 O003 -57.94(16) . . . . ?
C00E O004 C009 O005 64.02(15) . . . . ?
C00E O004 C009 C00F -178.85(13) . . . . ?
C00E C008 C00B O003 53.80(16) . . . . ?
C00E C008 C00G Br01 179.83(10) . . . . ?
C00F C00A C00C O005 -19.44(15) . . . . ?
C00F C00A C00C C00D -136.57(13) . . . . ?
C00F C00A C00C C00K 97.02(14) . . . . ?
C00G C008 C00B O003 169.56(12) . . . . ?
C00G C008 C00E O004 -171.92(12) . . . . ?
C00H C00I C00J C00K 3.3(2) . . . . ?
C00I C00J C00K C00C 5.9(3) . . . . ?
C00K C00C C00D C00H 7.7(2) . . . . ?
