#------------------------------------------------------------------------------
#$Date: 2020-03-04 08:12:43 +0200 (Wed, 04 Mar 2020) $
#$Revision: 248735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/61/7126110.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_7126110
loop_
_publ_author_name
'Wu, Ju'
'Abou-Hamdan, Hussein'
'Guillot, Régis'
'Kouklovsky, Cyrille'
'Vincent, Guillaume'
_publ_section_title
;
 Electrochemical synthesis of 3a-bromofuranoindolines and
 3a-bromopyrroloindolines mediated by MgBr₂.
;
_journal_issue                   11
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1713
_journal_page_last               1716
_journal_paper_doi               10.1039/c9cc09276e
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H25 Br N2 O6 S2 '
_chemical_formula_sum            'C26 H25 Br N2 O6 S2'
_chemical_formula_weight         605.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-04-17 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.761(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6142(9)
_cell_length_b                   15.2562(15)
_cell_length_c                   10.0113(10)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      66.72
_cell_measurement_theta_min      5.15
_cell_volume                     1312.9(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14066
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        66.959
_diffrn_reflns_theta_max         66.959
_diffrn_reflns_theta_min         4.426
_exptl_absorpt_coefficient_mu    4.001
_exptl_absorpt_correction_T_max  0.8816
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'apex3 Bruker'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_description       plate
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 2068 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         4552
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0227
_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)+(0.0321P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0562
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                4467
_reflns_number_total             4552
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09276e2.cif
_cod_data_source_block           8k
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7126110
_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.
;
_shelx_estimated_absorpt_t_min   0.631
_shelx_estimated_absorpt_t_max   0.909
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
C1 C 0.9736(5) 0.1647(2) 1.1070(4) 0.0333(8) Uani 1 1 d . . . . .
H1A H 0.886603 0.128608 1.133389 0.050 Uiso 1 1 calc R U . . .
H1B H 1.020235 0.195481 1.185693 0.050 Uiso 1 1 calc R U . . .
H1C H 1.051928 0.127186 1.069240 0.050 Uiso 1 1 calc R U . . .
C2 C 0.9148(3) 0.2310(3) 1.0032(3) 0.0220(6) Uani 1 1 d . . . . .
C3 C 0.9107(4) 0.3201(2) 1.0332(3) 0.0223(7) Uani 1 1 d . . . . .
H3 H 0.942469 0.339568 1.120882 0.027 Uiso 1 1 calc R U . . .
C4 C 0.8608(4) 0.3808(2) 0.9366(3) 0.0196(6) Uani 1 1 d . . . . .
H4 H 0.858303 0.441434 0.957848 0.023 Uiso 1 1 calc R U . . .
C5 C 0.8144(3) 0.3521(2) 0.8083(3) 0.0154(6) Uani 1 1 d . . . . .
C6 C 0.8149(4) 0.2635(2) 0.7763(3) 0.0197(7) Uani 1 1 d . . . . .
H6 H 0.781940 0.244312 0.688760 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8642(4) 0.2038(2) 0.8738(4) 0.0229(7) Uani 1 1 d . . . . .
H7 H 0.863839 0.143064 0.852708 0.028 Uiso 1 1 calc R U . . .
C8 C 0.4901(6) 0.8334(3) 0.8193(4) 0.0400(10) Uani 1 1 d . . . . .
H8A H 0.409614 0.877770 0.799318 0.060 Uiso 1 1 calc R U . . .
H8B H 0.593078 0.860409 0.815982 0.060 Uiso 1 1 calc R U . . .
H8C H 0.478751 0.809323 0.908811 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4732(5) 0.7608(2) 0.7172(4) 0.0279(8) Uani 1 1 d . . . . .
C10 C 0.3263(4) 0.7346(3) 0.6637(3) 0.0261(6) Uani 1 1 d . . . . .
H10 H 0.236135 0.764042 0.690115 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3106(4) 0.6660(2) 0.5725(3) 0.0215(7) Uani 1 1 d . . . . .
H11 H 0.210893 0.649197 0.534985 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4431(4) 0.62253(19) 0.5373(3) 0.0178(6) Uani 1 1 d . . . . .
C13 C 0.5904(4) 0.6492(2) 0.5859(3) 0.0223(7) Uani 1 1 d . . . . .
H13 H 0.680555 0.620465 0.557948 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6037(4) 0.7183(2) 0.6756(4) 0.0270(8) Uani 1 1 d . . . . .
H14 H 0.704082 0.736775 0.709211 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5013(4) 0.4703(2) 0.7958(3) 0.0154(6) Uani 1 1 d . . . . .
C16 C 0.5467(4) 0.5341(2) 0.8896(3) 0.0220(6) Uani 1 1 d . . . . .
H16 H 0.637516 0.568456 0.881258 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4525(4) 0.5452(2) 0.9966(3) 0.0269(8) Uani 1 1 d . . . . .
H17 H 0.480445 0.587578 1.063468 0.032 Uiso 1 1 calc R U . . .
C18 C 0.3184(4) 0.4955(2) 1.0072(3) 0.0272(8) Uani 1 1 d . . . . .
H18 H 0.256597 0.504364 1.081244 0.033 Uiso 1 1 calc R U . . .
C19 C 0.2737(4) 0.4334(2) 0.9116(3) 0.0215(7) Uani 1 1 d . . . . .
H19 H 0.181223 0.400200 0.918285 0.026 Uiso 1 1 calc R U . . .
C20 C 0.3673(3) 0.42069(19) 0.8058(3) 0.0145(6) Uani 1 1 d . . . . .
C21 C 0.3463(3) 0.35849(19) 0.6909(3) 0.0140(6) Uani 1 1 d . . . . .
C22 C 0.1890(3) 0.3592(2) 0.6125(3) 0.0171(6) Uani 1 1 d . . . . .
H22A H 0.102654 0.359113 0.672977 0.021 Uiso 1 1 calc R U . . .
H22B H 0.177545 0.308370 0.551187 0.021 Uiso 1 1 calc R U . . .
C23 C 0.1949(3) 0.4453(2) 0.5349(3) 0.0157(6) Uani 1 1 d . . . . .
H23 H 0.168252 0.496029 0.592283 0.019 Uiso 1 1 calc R U . . .
C24 C 0.4639(3) 0.39410(19) 0.5938(3) 0.0137(6) Uani 1 1 d . . . . .
H24 H 0.515790 0.346218 0.545096 0.016 Uiso 1 1 calc R U . . .
C25 C 0.0872(3) 0.4420(2) 0.4064(3) 0.0175(6) Uani 1 1 d . . . . .
C26 C -0.1053(4) 0.5163(3) 0.2766(4) 0.0257(7) Uani 1 1 d . . . . .
H26A H -0.176907 0.466322 0.274358 0.039 Uiso 1 1 calc R U . . .
H26B H -0.042926 0.514220 0.198302 0.039 Uiso 1 1 calc R U . . .
H26C H -0.165064 0.571007 0.275474 0.039 Uiso 1 1 calc R U . . .
N1 N 0.5756(3) 0.44727(16) 0.6774(2) 0.0150(5) Uani 1 1 d . . . . .
N2 N 0.3597(3) 0.44865(16) 0.5031(2) 0.0148(5) Uani 1 1 d . . . . .
O1 O 0.7936(3) 0.38986(15) 0.5550(2) 0.0204(5) Uani 1 1 d . . . . .
O2 O 0.8382(3) 0.51000(14) 0.7214(2) 0.0225(5) Uani 1 1 d . . . . .
O3 O 0.5757(3) 0.51129(15) 0.3846(2) 0.0225(5) Uani 1 1 d . . . . .
O4 O 0.3027(3) 0.55583(15) 0.3244(2) 0.0207(5) Uani 1 1 d . . . . .
O5 O 0.0866(3) 0.38330(16) 0.3274(2) 0.0252(5) Uani 1 1 d . . . . .
O6 O -0.0041(3) 0.51247(14) 0.3968(2) 0.0193(5) Uani 1 1 d . . . . .
S1 S 0.76564(8) 0.42897(5) 0.68070(7) 0.01548(16) Uani 1 1 d . . . . .
S2 S 0.42478(8) 0.53416(5) 0.42342(7) 0.01568(16) Uani 1 1 d . . . . .
Br Br 0.39918(3) 0.23874(2) 0.75354(3) 0.01948(9) 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 0.0181 0.0096 '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'
N N 0.0311 0.0189 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.5(3) . . ?
C3 C2 C1 121.1(3) . . ?
C7 C2 C1 120.4(4) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 S1 119.0(3) . . ?
C4 C5 S1 120.0(2) . . ?
C7 C6 C5 119.0(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.3(3) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 118.8(3) . . ?
C14 C9 C8 120.3(4) . . ?
C10 C9 C8 121.0(4) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 S2 119.3(2) . . ?
C13 C12 S2 119.4(3) . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C20 C15 C16 122.1(3) . . ?
C20 C15 N1 110.2(3) . . ?
C16 C15 N1 127.7(3) . . ?
C15 C16 C17 116.8(3) . . ?
C15 C16 H16 121.6 . . ?
C17 C16 H16 121.6 . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 118.4(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C15 120.5(3) . . ?
C19 C20 C21 129.1(3) . . ?
C15 C20 C21 110.5(3) . . ?
C20 C21 C22 116.9(2) . . ?
C20 C21 C24 102.1(2) . . ?
C22 C21 C24 105.7(2) . . ?
C20 C21 Br 109.23(19) . . ?
C22 C21 Br 110.5(2) . . ?
C24 C21 Br 112.16(19) . . ?
C21 C22 C23 102.2(2) . . ?
C21 C22 H22A 111.3 . . ?
C23 C22 H22A 111.3 . . ?
C21 C22 H22B 111.3 . . ?
C23 C22 H22B 111.3 . . ?
H22A C22 H22B 109.2 . . ?
N2 C23 C22 101.8(2) . . ?
N2 C23 C25 110.9(2) . . ?
C22 C23 C25 111.1(2) . . ?
N2 C23 H23 110.9 . . ?
C22 C23 H23 110.9 . . ?
C25 C23 H23 110.9 . . ?
N1 C24 N2 112.5(2) . . ?
N1 C24 C21 105.4(2) . . ?
N2 C24 C21 100.7(2) . . ?
N1 C24 H24 112.5 . . ?
N2 C24 H24 112.5 . . ?
C21 C24 H24 112.5 . . ?
O5 C25 O6 125.4(3) . . ?
O5 C25 C23 123.7(3) . . ?
O6 C25 C23 110.9(2) . . ?
O6 C26 H26A 109.5 . . ?
O6 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O6 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C15 N1 C24 107.2(2) . . ?
C15 N1 S1 121.4(2) . . ?
C24 N1 S1 121.7(2) . . ?
C23 N2 C24 113.5(2) . . ?
C23 N2 S2 119.7(2) . . ?
C24 N2 S2 121.8(2) . . ?
C25 O6 C26 114.6(3) . . ?
O1 S1 O2 121.07(14) . . ?
O1 S1 N1 106.01(13) . . ?
O2 S1 N1 105.79(13) . . ?
O1 S1 C5 108.32(14) . . ?
O2 S1 C5 106.82(14) . . ?
N1 S1 C5 108.30(13) . . ?
O3 S2 O4 120.56(14) . . ?
O3 S2 N2 106.50(13) . . ?
O4 S2 N2 105.04(13) . . ?
O3 S2 C12 108.56(15) . . ?
O4 S2 C12 107.48(14) . . ?
N2 S2 C12 108.14(14) . . ?
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
C1 C2 1.513(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.393(5) . ?
C2 C7 1.402(5) . ?
C3 C4 1.386(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(5) . ?
C5 S1 1.764(3) . ?
C6 C7 1.382(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.508(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.386(6) . ?
C9 C10 1.400(5) . ?
C10 C11 1.390(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(5) . ?
C12 S2 1.766(3) . ?
C13 C14 1.384(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.389(4) . ?
C15 C16 1.391(5) . ?
C15 N1 1.428(4) . ?
C16 C17 1.396(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.493(4) . ?
C21 C22 1.521(4) . ?
C21 C24 1.548(4) . ?
C21 Br 1.975(3) . ?
C22 C23 1.527(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 N2 1.476(4) . ?
C23 C25 1.537(4) . ?
C23 H23 1.0000 . ?
C24 N1 1.476(4) . ?
C24 N2 1.489(4) . ?
C24 H24 1.0000 . ?
C25 O5 1.195(4) . ?
C25 O6 1.332(4) . ?
C26 O6 1.440(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 S1 1.659(2) . ?
N2 S2 1.646(3) . ?
O1 S1 1.427(2) . ?
O2 S1 1.432(2) . ?
O3 S2 1.424(2) . ?
O4 S2 1.436(2) . ?
