#------------------------------------------------------------------------------
#$Date: 2016-11-06 04:00:53 +0200 (Sun, 06 Nov 2016) $
#$Revision: 187953 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/36/1543680.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_1543680
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 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.5580(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.2273(2)
_cell_length_b                   23.0379(11)
_cell_length_c                   15.5364(8)
_cell_measurement_reflns_used    4320
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3594
_cell_measurement_theta_min      2.6344
_cell_volume                     1862.19(15)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16224
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.357
_exptl_absorpt_correction_T_max  0.9486
_exptl_absorpt_correction_T_min  0.8964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Acicular
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.608
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.164
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0893P)²+3.6030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1745
_reflns_number_gt                3114
_reflns_number_total             3807
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01408_si_004.cif
_cod_data_source_block           110208lt_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               1543680
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.0785(6) 0.15909(13) 0.63885(19) 0.0152(6) Uani 1 1 d .
C2 C 0.3801(6) 0.09804(13) 0.6006(2) 0.0161(6) Uani 1 1 d .
C3 C -0.2162(6) 0.24546(13) 0.5456(2) 0.0147(6) Uani 1 1 d .
C4 C -0.3797(6) 0.28285(13) 0.4942(2) 0.0173(6) Uani 1 1 d .
C5 C -0.3791(6) 0.28434(14) 0.4053(2) 0.0194(7) Uani 1 1 d .
H5 H -0.4960 0.3086 0.3714 0.023 Uiso 1 1 calc R
C6 C -0.2063(6) 0.25002(14) 0.3662(2) 0.0194(7) Uani 1 1 d .
H6 H -0.2048 0.2509 0.3051 0.023 Uiso 1 1 calc R
C7 C -0.0355(6) 0.21448(14) 0.4154(2) 0.0173(6) Uani 1 1 d .
H7 H 0.0861 0.1921 0.3879 0.021 Uiso 1 1 calc R
C8 C -0.0409(5) 0.21127(13) 0.5047(2) 0.0147(6) Uani 1 1 d .
C9 C 0.3133(6) 0.13428(13) 0.5292(2) 0.0145(6) Uani 1 1 d .
C10 C 0.4398(6) 0.12892(13) 0.4550(2) 0.0152(6) Uani 1 1 d .
H10 H 0.3995 0.1534 0.4064 0.018 Uiso 1 1 calc R
C11 C 0.6297(6) 0.08588(13) 0.4548(2) 0.0165(6) Uani 1 1 d .
C12 C 0.6941(6) 0.05070(13) 0.5264(2) 0.0180(6) Uani 1 1 d .
H12 H 0.8247 0.0222 0.5240 0.022 Uiso 1 1 calc R
C13 C 0.5715(6) 0.05633(13) 0.6013(2) 0.0175(6) Uani 1 1 d .
H13 H 0.6165 0.0328 0.6507 0.021 Uiso 1 1 calc R
C14 C 0.7683(6) 0.07641(13) 0.3769(2) 0.0181(6) Uani 1 1 d .
C15 C 0.8278(8) 0.11050(17) 0.2371(2) 0.0312(9) Uani 1 1 d .
H15A H 1.0099 0.1181 0.2547 0.047 Uiso 1 1 calc R
H15B H 0.7608 0.1403 0.1959 0.047 Uiso 1 1 calc R
H15C H 0.8093 0.0722 0.2099 0.047 Uiso 1 1 calc R
C16 C 0.2329(6) 0.08496(14) 0.7498(2) 0.0183(6) Uani 1 1 d .
H16A H 0.2213 0.0425 0.7409 0.022 Uiso 1 1 calc R
H16B H 0.0795 0.0973 0.7778 0.022 Uiso 1 1 calc R
C17 C 0.4717(7) 0.09844(15) 0.8100(2) 0.0236(7) Uani 1 1 d .
H17A H 0.4802 0.1406 0.8222 0.028 Uiso 1 1 calc R
H17B H 0.6269 0.0874 0.7821 0.028 Uiso 1 1 calc R
C18 C 0.4643(11) 0.0649(2) 0.8946(3) 0.0528(13) Uani 1 1 d .
H18A H 0.6227 0.0740 0.9324 0.063 Uiso 1 1 calc R
H18B H 0.3169 0.0793 0.9240 0.063 Uiso 1 1 calc R
C19 C 0.6840(11) -0.0230(3) 0.8761(4) 0.0761(19) Uani 1 1 d .
H19A H 0.7427 -0.0110 0.8208 0.114 Uiso 1 1 calc R
H19B H 0.6618 -0.0653 0.8765 0.114 Uiso 1 1 calc R
H19C H 0.8118 -0.0117 0.9234 0.114 Uiso 1 1 calc R
N1 N 0.2298(5) 0.11352(11) 0.66536(17) 0.0159(5) Uani 1 1 d .
N2 N 0.1189(5) 0.17180(11) 0.55433(16) 0.0138(5) Uani 1 1 d .
N3 N -0.0814(5) 0.18354(11) 0.68723(17) 0.0168(6) Uani 1 1 d .
O5 O 0.4436(7) 0.00450(15) 0.8873(2) 0.0549(9) Uani 1 1 d .
O1 O -0.1092(4) 0.29122(10) 0.69835(15) 0.0222(5) Uani 1 1 d .
O2 O -0.4978(4) 0.23270(10) 0.67445(15) 0.0199(5) Uani 1 1 d .
O3 O 0.9359(5) 0.04086(11) 0.37167(16) 0.0260(6) Uani 1 1 d .
O4 O 0.6857(5) 0.11197(11) 0.31227(16) 0.0256(6) Uani 1 1 d .
S1 S -0.23456(14) 0.24130(3) 0.65855(5) 0.0141(2) Uani 1 1 d .
Cl1 Cl -0.58979(16) 0.32904(4) 0.54007(5) 0.0245(2) 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
N3 C1 N1 123.2(3)
N3 C1 N2 128.4(3)
N1 C1 N2 108.3(3)
N1 C2 C13 129.3(3)
N1 C2 C9 107.8(3)
C13 C2 C9 122.8(3)
C8 C3 C4 118.3(3)
C8 C3 S1 121.2(2)
C4 C3 S1 120.5(2)
C5 C4 C3 121.5(3)
C5 C4 Cl1 117.4(2)
C3 C4 Cl1 121.1(2)
C4 C5 C6 119.3(3)
C4 C5 H5 120.4
C6 C5 H5 120.4
C5 C6 C7 120.6(3)
C5 C6 H6 119.7
C7 C6 H6 119.7
C6 C7 C8 120.4(3)
C6 C7 H7 119.8
C8 C7 H7 119.8
C7 C8 C3 119.8(3)
C7 C8 N2 120.7(3)
C3 C8 N2 119.4(3)
C10 C9 C2 120.0(3)
C10 C9 N2 134.0(3)
C2 C9 N2 105.9(3)
C9 C10 C11 117.3(3)
C9 C10 H10 121.3
C11 C10 H10 121.3
C12 C11 C10 121.7(3)
C12 C11 C14 117.8(3)
C10 C11 C14 120.5(3)
C13 C12 C11 121.4(3)
C13 C12 H12 119.3
C11 C12 H12 119.3
C2 C13 C12 116.7(3)
C2 C13 H13 121.6
C12 C13 H13 121.6
O3 C14 O4 123.3(3)
O3 C14 C11 124.6(3)
O4 C14 C11 112.0(3)
O4 C15 H15A 109.5
O4 C15 H15B 109.5
H15A C15 H15B 109.5
O4 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
N1 C16 C17 113.4(3)
N1 C16 H16A 108.9
C17 C16 H16A 108.9
N1 C16 H16B 108.9
C17 C16 H16B 108.9
H16A C16 H16B 107.7
C16 C17 C18 109.8(3)
C16 C17 H17A 109.7
C18 C17 H17A 109.7
C16 C17 H17B 109.7
C18 C17 H17B 109.7
H17A C17 H17B 108.2
O5 C18 C17 116.2(4)
O5 C18 H18A 108.2
C17 C18 H18A 108.2
O5 C18 H18B 108.2
C17 C18 H18B 108.2
H18A C18 H18B 107.4
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
C1 N1 C2 109.6(3)
C1 N1 C16 125.1(3)
C2 N1 C16 125.3(3)
C1 N2 C8 121.2(2)
C1 N2 C9 108.2(2)
C8 N2 C9 130.1(3)
C1 N3 S1 122.1(2)
C18 O5 C19 112.8(4)
C14 O4 C15 116.1(3)
O1 S1 O2 116.26(14)
O1 S1 N3 110.65(14)
O2 S1 N3 107.49(14)
O1 S1 C3 108.54(14)
O2 S1 C3 108.85(14)
N3 S1 C3 104.39(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N3 1.305(4)
C1 N1 1.354(4)
C1 N2 1.382(4)
C2 N1 1.382(4)
C2 C13 1.386(4)
C2 C9 1.405(4)
C3 C8 1.406(4)
C3 C4 1.406(4)
C3 S1 1.770(3)
C4 C5 1.381(4)
C4 Cl1 1.732(3)
C5 C6 1.384(5)
C5 H5 0.9500
C6 C7 1.385(4)
C6 H6 0.9500
C7 C8 1.393(4)
C7 H7 0.9500
C8 N2 1.412(4)
C9 C10 1.388(4)
C9 N2 1.417(4)
C10 C11 1.403(4)
C10 H10 0.9500
C11 C12 1.391(4)
C11 C14 1.486(4)
C12 C13 1.388(5)
C12 H12 0.9500
C13 H13 0.9500
C14 O3 1.208(4)
C14 O4 1.335(4)
C15 O4 1.443(4)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 N1 1.467(4)
C16 C17 1.518(4)
C16 H16A 0.9900
C16 H16B 0.9900
C17 C18 1.528(6)
C17 H17A 0.9900
C17 H17B 0.9900
C18 O5 1.399(6)
C18 H18A 0.9900
C18 H18B 0.9900
C19 O5 1.433(7)
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
N3 S1 1.594(3)
O1 S1 1.434(2)
O2 S1 1.435(2)
