#------------------------------------------------------------------------------
#$Date: 2019-11-04 11:23:46 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222593 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/40/4034033.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_4034033
loop_
_publ_author_name
'Sen, Chiranjit'
'Sahoo, Tapan'
'Singh, Harshvardhan'
'Suresh, Eringathodi'
'Ghosh, Subhash Chandra'
_publ_section_title
;
 Visible Light-Promoted Photocatalytic C-5 Carboxylation of
 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer
 Pathway.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9869
_journal_page_last               9896
_journal_paper_doi               10.1021/acs.joc.9b00942
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C17 H9 F5 N2 O4 S'
_chemical_formula_weight         432.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 107.106(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.1706(15)
_cell_length_b                   12.5910(10)
_cell_length_c                   17.2521(14)
_cell_measurement_reflns_used    9829
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      31.5314
_cell_measurement_theta_min      2.4704
_cell_volume                     3357.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33197
_diffrn_reflns_theta_full        31.55
_diffrn_reflns_theta_max         31.55
_diffrn_reflns_theta_min         2.22
_diffrn_source_type              'MICRO FOCUS TUBE'
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.9520
_exptl_absorpt_correction_T_min  0.9170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.384
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         5549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0319
_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)+(0.0528P)²+2.1088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                5147
_reflns_number_total             5549
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b00942_si_004.cif
_cod_data_source_block           BRR169SG
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4034033
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
O O2 0.68347(5) 0.64125(6) 0.33029(4) 0.02478(15) Uani d . . 1
N N2 0.90379(5) 0.40970(7) 0.52113(5) 0.02065(15) Uani d . . 1
C C2 0.79397(7) 0.40035(7) 0.15358(6) 0.02387(19) Uani d . . 1
F F2 0.85979(5) 0.36868(6) 0.12772(5) 0.03562(17) Uani d . . 1
S S1 0.76343(2) 0.59589(2) 0.32873(2) 0.01870(7) Uani d . . 1
H H1 0.8559(11) 0.5126(13) 0.4202(10) 0.036(4) Uiso d . . 1
N N1 0.80425(5) 0.52969(7) 0.41131(5) 0.02032(15) Uani d . . 1
C C1 0.80849(6) 0.46483(7) 0.22088(6) 0.02039(17) Uani d . . 1
F F1 0.89033(4) 0.48982(5) 0.25961(5) 0.02957(15) Uani d . . 1
O O1 0.83180(5) 0.66146(6) 0.31930(4) 0.02433(15) Uani d . . 1
F F3 0.69574(6) 0.30861(6) 0.04737(4) 0.03717(17) Uani d . . 1
C C3 0.71081(7) 0.36988(8) 0.11281(6) 0.02531(19) Uani d . . 1
O O3 0.68906(5) 0.21032(6) 0.65642(5) 0.02636(15) Uani d . . 1
O O4 0.57542(5) 0.31821(6) 0.60810(5) 0.02744(16) Uani d . . 1
C C4 0.64327(7) 0.40259(8) 0.14034(6) 0.02411(19) Uani d . . 1
F F4 0.56283(5) 0.37234(6) 0.10109(5) 0.03750(17) Uani d . . 1
C C15 0.81883(6) 0.40666(7) 0.51831(5) 0.01620(15) Uani d . . 1
C C9 0.64270(6) 0.40909(7) 0.50074(6) 0.01912(16) Uani d . . 1
H H9 0.582258 0.409704 0.494101 0.023 Uiso calc U R 1
C C8 0.67459(6) 0.47011(7) 0.44743(5) 0.01964(16) Uani d . . 1
H H8 0.636302 0.511144 0.405917 0.024 Uiso calc U R 1
C C7 0.76159(6) 0.46953(7) 0.45621(5) 0.01697(15) Uani d . . 1
C C6 0.74108(6) 0.50253(7) 0.24818(5) 0.01773(15) Uani d . . 1
F F5 0.58967(4) 0.49543(6) 0.23114(4) 0.03020(14) Uani d . . 1
C C5 0.65787(6) 0.46775(7) 0.20748(6) 0.02047(17) Uani d . . 1
C C14 0.95871(6) 0.35432(9) 0.57826(6) 0.02453(18) Uani d . . 1
H H14 1.017985 0.354294 0.580019 0.029 Uiso calc U R 1
C C10 0.69534(6) 0.34856(7) 0.56210(5) 0.01703(15) Uani d . . 1
C C13 0.93380(7) 0.29518(9) 0.63680(6) 0.02504(19) Uani d . . 1
H H13 0.976086 0.258262 0.677966 0.03 Uiso calc U R 1
C C11 0.78637(6) 0.34652(7) 0.57248(5) 0.01630(15) Uani d . . 1
C C12 0.84873(6) 0.29090(8) 0.63437(5) 0.02079(17) Uani d . . 1
H H12 0.831439 0.251086 0.673738 0.025 Uiso calc U R 1
C C17 0.52912(8) 0.25567(10) 0.65199(9) 0.0360(3) Uani d . . 1
H H17A 0.47148 0.286145 0.6442 0.054 Uiso calc U R 1
H H17B 0.561056 0.25592 0.709869 0.054 Uiso calc U R 1
H H17C 0.523428 0.182533 0.631673 0.054 Uiso calc U R 1
C C16 0.65555(6) 0.28423(7) 0.61416(5) 0.01965(16) Uani d . . 1
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C14 N2 C15 117.64(8)
F2 C2 C3 120.19(10)
F2 C2 C1 120.26(10)
C3 C2 C1 119.55(9)
O2 S1 O1 120.63(5)
O2 S1 N1 109.20(4)
O1 S1 N1 105.66(4)
O2 S1 C6 107.71(5)
O1 S1 C6 106.27(4)
N1 S1 C6 106.58(4)
C7 N1 S1 128.81(7)
C7 N1 H1 112.9(12)
S1 N1 H1 115.1(12)
F1 C1 C2 117.33(9)
F1 C1 C6 120.71(9)
C2 C1 C6 121.96(9)
F3 C3 C4 120.07(10)
F3 C3 C2 120.21(10)
C4 C3 C2 119.72(9)
C16 O4 C17 115.07(9)
F4 C4 C3 119.62(10)
F4 C4 C5 119.73(10)
C3 C4 C5 120.65(9)
N2 C15 C11 123.84(8)
N2 C15 C7 115.79(8)
C11 C15 C7 120.37(8)
C10 C9 C8 122.82(9)
C10 C9 H9 118.6
C8 C9 H9 118.6
C7 C8 C9 119.12(8)
C7 C8 H8 120.4
C9 C8 H8 120.4
C8 C7 N1 126.33(8)
C8 C7 C15 120.18(8)
N1 C7 C15 113.43(8)
C1 C6 C5 117.31(9)
C1 C6 S1 119.45(7)
C5 C6 S1 123.17(7)
F5 C5 C4 117.40(9)
F5 C5 C6 121.88(9)
C4 C5 C6 120.72(9)
N2 C14 C13 123.08(9)
N2 C14 H14 118.5
C13 C14 H14 118.5
C9 C10 C11 119.14(8)
C9 C10 C16 119.06(8)
C11 C10 C16 121.76(8)
C12 C13 C14 119.88(9)
C12 C13 H13 120.1
C14 C13 H13 120.1
C15 C11 C12 116.14(8)
C15 C11 C10 118.35(8)
C12 C11 C10 125.49(8)
C13 C12 C11 119.36(9)
C13 C12 H12 120.3
C11 C12 H12 120.3
O4 C17 H17A 109.5
O4 C17 H17B 109.5
H17A C17 H17B 109.5
O4 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
O3 C16 O4 123.05(9)
O3 C16 C10 125.91(9)
O4 C16 C10 111.05(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 S1 1.4209(8)
N2 C14 1.3158(12)
N2 C15 1.3608(12)
C2 F2 1.3306(11)
C2 C3 1.3762(16)
C2 C1 1.3790(14)
S1 O1 1.4269(7)
S1 N1 1.6145(8)
S1 C6 1.7744(9)
N1 C7 1.4015(11)
N1 H1 0.832(17)
C1 F1 1.3330(11)
C1 C6 1.3918(13)
F3 C3 1.3296(12)
C3 C4 1.3758(15)
O3 C16 1.2079(12)
O4 C16 1.3391(12)
O4 C17 1.4447(13)
C4 F4 1.3332(12)
C4 C5 1.3819(14)
C15 C11 1.4180(12)
C15 C7 1.4309(12)
C9 C10 1.3770(13)
C9 C8 1.4075(13)
C9 H9 0.95
C8 C7 1.3700(12)
C8 H8 0.95
C6 C5 1.3927(13)
F5 C5 1.3302(11)
C14 C13 1.4057(14)
C14 H14 0.95
C10 C11 1.4299(12)
C10 C16 1.4887(12)
C13 C12 1.3649(14)
C13 H13 0.95
C11 C12 1.4192(12)
C12 H12 0.95
C17 H17A 0.98
C17 H17B 0.98
C17 H17C 0.98
