An Organic Intermolecular Dehydrogenative Annulation Reaction.
Maiti, Saikat; Achar, Tapas Kumar; Mal, Prasenjit; Organic letters 19 (2017) 2006–2009; doi:10.1021/acs.orglett.7b00562

data_1545746
_publ_section_title
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 An Organic Intermolecular Dehydrogenative Annulation Reaction.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2006
_journal_page_last               2009
_journal_paper_doi               10.1021/acs.orglett.7b00562
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C19 H13 Br N2 O5 S'
_chemical_formula_sum            'C19 H13 Br N2 O5 S'
_chemical_formula_weight         461.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-01-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_cell_angle_alpha                103.152(9)
_cell_angle_beta                 108.554(9)
_cell_angle_gamma                99.041(9)
_cell_formula_units_Z            4
_cell_length_a                   10.752(2)
_cell_length_b                   12.403(2)
_cell_length_c                   14.821(2)
_cell_measurement_reflns_used    3168
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.66
_cell_volume                     1767.3(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17141
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.340
_diffrn_reflns_theta_max         25.340
_diffrn_reflns_theta_min         1.517
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.481
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0790 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.7941.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         6431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0480
_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/[\s^2^(Fo^2^)+(0.0543P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1236
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4208
_reflns_number_total             6431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00562_si_001.cif
_cod_data_source_block           pmal_sm_2_217_0m
_cod_depositor_comments
'Adding full bibliography for 1545745--1545747.cif.'
_cod_original_cell_volume        1767.4(6)
_cod_database_code               1545746
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12E(H12E), C2BP(H2BP), C2GS(H2GS), C4EN(H4EN), C8VK(H8VK), C8NN(H8NN),
 C02(H02), C03(H03), C06(H06), C08(H08), C1SE(H1SE), C1CK(H1CK), C2GK(H2GK),
 C2UT(H2UT), C4UO(H4UO), C4QQ(H4QQ), C7TK(H7TK), C37E(H37E), C38E(H38E),
 C39E(H39E)
2.b Idealised Me refined as rotating group:
 C05(H05A,H05B,H05C), C8ON(H8OA,H8OB,H8OC)
;
_shelx_res_checksum              97040
_shelx_hkl_checksum              71247
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'