#------------------------------------------------------------------------------
#$Date: 2016-11-06 04:00:53 +0200 (Sun, 06 Nov 2016) $
#$Revision: 187953 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/36/1543678.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_1543678
loop_
_publ_author_name
'Dalvi, Prashant B.'
'Lin, Kuang-Ling'
'Kulkarni, Manohar V.'
'Sun, Chung-Ming'
_publ_section_title
;
 Rhodium-Catalyzed Regioselective Synthesis of Isocoumarins through
 Benzothiadiazine-Fused Frameworks.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3706
_journal_page_last               3709
_journal_paper_doi               10.1021/acs.orglett.6b01408
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C19 H18 Cl N3 O5 S'
_chemical_formula_weight         435.87
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.7460(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4885(3)
_cell_length_b                   12.1708(4)
_cell_length_c                   14.9547(4)
_cell_measurement_reflns_used    8579
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.4219
_cell_measurement_theta_min      2.1654
_cell_volume                     1891.60(10)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_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       'φ and ω 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  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0295
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16702
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Tabullar
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0647P)²+0.1266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                3436
_reflns_number_total             3868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01408_si_002.cif
_cod_data_source_block           100940lt_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1543677--1543680.cif.
;
_cod_database_code               1543678
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.00128(15) 0.26207(13) 0.14526(10) 0.0136(3) Uani 1 1 d .
C2 C 0.08952(16) 0.18326(14) 0.17880(10) 0.0164(3) Uani 1 1 d .
H2 H 0.0684 0.1074 0.1733 0.020 Uiso 1 1 calc R
C3 C 0.21024(16) 0.21633(13) 0.22085(11) 0.0171(4) Uani 1 1 d .
H3 H 0.2712 0.1626 0.2447 0.020 Uiso 1 1 calc R
C4 C 0.24190(15) 0.32602(14) 0.22819(11) 0.0168(3) Uani 1 1 d .
H4 H 0.3248 0.3465 0.2570 0.020 Uiso 1 1 calc R
C5 C 0.15475(15) 0.40870(13) 0.19416(10) 0.0134(3) Uani 1 1 d .
C6 C 0.12291(14) 0.59293(13) 0.16929(10) 0.0121(3) Uani 1 1 d .
C7 C 0.05240(14) 0.76177(13) 0.12420(10) 0.0119(3) Uani 1 1 d .
C8 C 0.03971(15) 0.87366(13) 0.10816(10) 0.0135(3) Uani 1 1 d .
H8 H 0.1077 0.9235 0.1270 0.016 Uiso 1 1 calc R
C9 C -0.07756(15) 0.90920(13) 0.06308(10) 0.0144(3) Uani 1 1 d .
H9 H -0.0902 0.9855 0.0517 0.017 Uiso 1 1 calc R
C10 C -0.17724(14) 0.83634(13) 0.03396(10) 0.0134(3) Uani 1 1 d .
C11 C -0.16433(15) 0.72333(13) 0.05059(10) 0.0128(3) Uani 1 1 d .
H11 H -0.2318 0.6730 0.0314 0.015 Uiso 1 1 calc R
C12 C -0.04842(15) 0.68934(13) 0.09636(10) 0.0117(3) Uani 1 1 d .
C13 C 0.03171(14) 0.37473(13) 0.15187(10) 0.0127(3) Uani 1 1 d .
C14 C 0.28119(14) 0.74607(14) 0.20491(10) 0.0145(3) Uani 1 1 d .
H14A H 0.3232 0.6943 0.2508 0.017 Uiso 1 1 calc R
H14B H 0.2684 0.8165 0.2356 0.017 Uiso 1 1 calc R
C15 C 0.37000(15) 0.76527(14) 0.13374(11) 0.0171(3) Uani 1 1 d .
H15A H 0.3235 0.8085 0.0835 0.021 Uiso 1 1 calc R
H15B H 0.4451 0.8090 0.1606 0.021 Uiso 1 1 calc R
C16 C 0.41702(15) 0.65949(14) 0.09669(10) 0.0175(3) Uani 1 1 d .
H16A H 0.3429 0.6134 0.0719 0.021 Uiso 1 1 calc R
H16B H 0.4687 0.6756 0.0475 0.021 Uiso 1 1 calc R
C17 C 0.51546(18) 0.49233(16) 0.14462(13) 0.0276(4) Uani 1 1 d .
H17A H 0.4328 0.4547 0.1295 0.041 Uiso 1 1 calc R
H17B H 0.5660 0.4553 0.1958 0.041 Uiso 1 1 calc R
H17C H 0.5628 0.4906 0.0924 0.041 Uiso 1 1 calc R
C18 C -0.29558(15) 0.88304(14) -0.01800(10) 0.0156(3) Uani 1 1 d .
C19 C -0.50395(16) 0.84616(16) -0.09213(12) 0.0242(4) Uani 1 1 d .
H19A H -0.5440 0.9030 -0.0588 0.036 Uiso 1 1 calc R
H19B H -0.5641 0.7848 -0.1054 0.036 Uiso 1 1 calc R
H19C H -0.4824 0.8770 -0.1487 0.036 Uiso 1 1 calc R
Cl1 Cl -0.14989(4) 0.21848(3) 0.09604(3) 0.01697(13) Uani 1 1 d .
N1 N 0.19793(12) 0.51575(11) 0.20447(8) 0.0142(3) Uani 1 1 d .
N2 N 0.15514(12) 0.70170(11) 0.16737(8) 0.0122(3) Uani 1 1 d .
N3 N -0.00279(12) 0.58406(11) 0.12563(8) 0.0116(3) Uani 1 1 d .
O1 O -0.17578(10) 0.47497(9) 0.18595(7) 0.0165(3) Uani 1 1 d .
O2 O -0.14699(11) 0.45989(9) 0.02700(7) 0.0173(3) Uani 1 1 d .
O3 O 0.49352(11) 0.60297(10) 0.16796(8) 0.0201(3) Uani 1 1 d .
O4 O -0.30813(12) 0.97815(10) -0.04112(9) 0.0257(3) Uani 1 1 d .
O5 O -0.38797(11) 0.80719(10) -0.03817(7) 0.0180(3) Uani 1 1 d .
S1 S -0.09047(3) 0.46981(3) 0.11910(2) 0.01141(12) 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'
N N 0.0061 0.0033 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 C13 121.12(15)
C2 C1 Cl1 118.07(13)
C13 C1 Cl1 120.80(12)
C1 C2 C3 119.14(15)
C1 C2 H2 120.4
C3 C2 H2 120.4
C4 C3 C2 120.69(15)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 121.77(15)
C3 C4 H4 119.1
C5 C4 H4 119.1
N1 C5 C4 116.54(14)
N1 C5 C13 126.09(14)
C4 C5 C13 117.37(15)
N1 C6 N2 125.04(14)
N1 C6 N3 128.34(15)
N2 C6 N3 106.61(13)
C8 C7 N2 130.45(14)
C8 C7 C12 121.16(14)
N2 C7 C12 108.39(14)
C7 C8 C9 116.61(14)
C7 C8 H8 121.7
C9 C8 H8 121.7
C8 C9 C10 122.05(15)
C8 C9 H9 119.0
C10 C9 H9 119.0
C9 C10 C11 121.21(14)
C9 C10 C18 117.27(14)
C11 C10 C18 121.49(14)
C12 C11 C10 116.18(14)
C12 C11 H11 121.9
C10 C11 H11 121.9
C11 C12 C7 122.77(15)
C11 C12 N3 131.67(14)
C7 C12 N3 105.56(13)
C1 C13 C5 119.91(14)
C1 C13 S1 118.33(12)
C5 C13 S1 121.35(12)
N2 C14 C15 113.15(12)
N2 C14 H14A 108.9
C15 C14 H14A 108.9
N2 C14 H14B 108.9
C15 C14 H14B 108.9
H14A C14 H14B 107.8
C16 C15 C14 112.71(14)
C16 C15 H15A 109.1
C14 C15 H15A 109.1
C16 C15 H15B 109.1
C14 C15 H15B 109.1
H15A C15 H15B 107.8
O3 C16 C15 108.45(13)
O3 C16 H16A 110.0
C15 C16 H16A 110.0
O3 C16 H16B 110.0
C15 C16 H16B 110.0
H16A C16 H16B 108.4
O3 C17 H17A 109.5
O3 C17 H17B 109.5
H17A C17 H17B 109.5
O3 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O4 C18 O5 123.09(15)
O4 C18 C10 124.50(15)
O5 C18 C10 112.41(14)
O5 C19 H19A 109.5
O5 C19 H19B 109.5
H19A C19 H19B 109.5
O5 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C6 N1 C5 117.92(13)
C6 N2 C7 109.95(13)
C6 N2 C14 124.09(13)
C7 N2 C14 125.95(13)
C6 N3 C12 109.48(12)
C6 N3 S1 124.95(11)
C12 N3 S1 125.26(10)
C17 O3 C16 111.65(13)
C18 O5 C19 115.29(13)
O2 S1 O1 117.39(7)
O2 S1 N3 106.35(7)
O1 S1 N3 108.39(7)
O2 S1 C13 114.06(7)
O1 S1 C13 109.72(7)
N3 S1 C13 99.12(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.380(2)
C1 C13 1.408(2)
C1 Cl1 1.7385(16)
C2 C3 1.395(2)
C2 H2 0.9500
C3 C4 1.377(2)
C3 H3 0.9500
C4 C5 1.408(2)
C4 H4 0.9500
C5 N1 1.381(2)
C5 C13 1.420(2)
C6 N1 1.291(2)
C6 N2 1.368(2)
C6 N3 1.3943(19)
C7 C8 1.386(2)
C7 N2 1.3874(19)
C7 C12 1.396(2)
C8 C9 1.390(2)
C8 H8 0.9500
C9 C10 1.395(2)
C9 H9 0.9500
C10 C11 1.401(2)
C10 C18 1.486(2)
C11 C12 1.376(2)
C11 H11 0.9500
C12 N3 1.416(2)
C13 S1 1.7470(15)
C14 N2 1.4679(19)
C14 C15 1.524(2)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.510(2)
C15 H15A 0.9900
C15 H15B 0.9900
C16 O3 1.4221(19)
C16 H16A 0.9900
C16 H16B 0.9900
C17 O3 1.418(2)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 O4 1.210(2)
C18 O5 1.343(2)
C19 O5 1.4461(19)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
N3 S1 1.6627(13)
O1 S1 1.4300(12)
O2 S1 1.4293(11)
