#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/94/2239449.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239449
loop_
_publ_author_name
'Gopinath, S.'
'Sethusankar, K.'
'Saravanan, Velu'
'Mohanakrishnan, Arasambattu K.'
_publ_section_title
;
 2-(4-Fluoro-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde
;
_journal_coeditor_code           SU2695
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o273
_journal_page_last               o274
_journal_paper_doi               10.1107/S1600536814002633
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C25 H15 F N2 O6 S'
_chemical_formula_moiety         'C25 H15 F N2 O6 S'
_chemical_formula_sum            'C25 H15 F N2 O6 S'
_chemical_formula_weight         490.45
_chemical_name_systematic
2-(4-Fluoro-2-nitrophenyl)-4-hydroxy-9-phenylsulfonyl-9H-carbazole-3-carbaldehyde
_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                 93.820(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.124(5)
_cell_length_b                   14.191(5)
_cell_length_c                   18.607(5)
_cell_measurement_reflns_used    7207
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.69
_cell_measurement_theta_min      2.19
_cell_volume                     2140.4(16)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Brukker Kappa APEXII CCD'
_diffrn_measurement_method       'ω & φ 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  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0353
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            31082
_diffrn_reflns_theta_full        31.69
_diffrn_reflns_theta_max         31.69
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         7207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0477
_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)+(0.0698P)²+0.4156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                4725
_reflns_number_total             7207
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2695sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239449
_cod_database_fobs_code          2239449
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_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
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.22774(18) 0.88060(12) -0.01369(8) 0.0374(3) Uani d . 1 1
C C2 0.1387(2) 0.83895(14) -0.07118(9) 0.0495(4) Uani d . 1 1
H H2 0.1307 0.7738 -0.0757 0.059 Uiso calc R 1 1
C C3 0.0621(2) 0.89880(16) -0.12166(10) 0.0566(5) Uani d . 1 1
H H3 -0.0006 0.8729 -0.1604 0.068 Uiso calc R 1 1
C C4 0.0754(2) 0.99483(15) -0.11661(10) 0.0552(5) Uani d . 1 1
H H4 0.0208 1.0325 -0.1514 0.066 Uiso calc R 1 1
C C5 0.1683(2) 1.03627(14) -0.06079(9) 0.0482(4) Uani d . 1 1
H H5 0.1798 1.1014 -0.0582 0.058 Uiso calc R 1 1
C C6 0.24489(19) 0.97816(12) -0.00809(8) 0.0378(3) Uani d . 1 1
C C7 0.33800(19) 0.99774(11) 0.05859(8) 0.0361(3) Uani d . 1 1
C C8 0.37439(17) 0.91229(10) 0.09332(8) 0.0338(3) Uani d . 1 1
C C9 0.45053(19) 0.90720(11) 0.16234(8) 0.0368(3) Uani d . 1 1
H H9 0.4734 0.8494 0.1843 0.044 Uiso calc R 1 1
C C10 0.49084(19) 0.99004(11) 0.19702(8) 0.0366(3) Uani d . 1 1
C C11 0.4656(2) 1.07785(11) 0.16215(9) 0.0412(4) Uani d . 1 1
C C12 0.3891(2) 1.08113(11) 0.09237(9) 0.0408(4) Uani d . 1 1
C C13 0.5105(3) 1.16400(13) 0.19907(11) 0.0577(5) Uani d . 1 1
H H13 0.5595 1.1591 0.2455 0.069 Uiso calc R 1 1
C C14 0.10618(19) 0.73000(10) 0.11778(9) 0.0380(3) Uani d . 1 1
C C15 0.1077(2) 0.76246(12) 0.18780(10) 0.0470(4) Uani d . 1 1
H H15 0.2061 0.7803 0.2125 0.056 Uiso calc R 1 1
C C16 -0.0402(3) 0.76793(15) 0.22048(13) 0.0623(5) Uani d . 1 1
H H16 -0.0425 0.7906 0.2673 0.075 Uiso calc R 1 1
C C17 -0.1846(3) 0.73945(18) 0.18295(16) 0.0730(7) Uani d . 1 1
H H17 -0.2839 0.7433 0.2049 0.088 Uiso calc R 1 1
C C18 -0.1833(3) 0.70603(18) 0.11453(15) 0.0729(7) Uani d . 1 1
H H18 -0.2812 0.6863 0.0905 0.087 Uiso calc R 1 1
C C19 -0.0383(2) 0.70121(14) 0.08066(12) 0.0558(5) Uani d . 1 1
H H19 -0.0374 0.6790 0.0337 0.067 Uiso calc R 1 1
C C20 0.55668(19) 0.98415(11) 0.27357(8) 0.0367(3) Uani d . 1 1
C C21 0.7260(2) 0.98788(14) 0.29145(10) 0.0503(4) Uani d . 1 1
H H21 0.7975 0.9992 0.2554 0.060 Uiso calc R 1 1
C C22 0.7897(2) 0.97524(15) 0.36099(11) 0.0550(5) Uani d . 1 1
H H22 0.9028 0.9789 0.3721 0.066 Uiso calc R 1 1
C C23 0.6842(2) 0.95715(13) 0.41362(10) 0.0500(4) Uani d . 1 1
C C24 0.5168(2) 0.95119(12) 0.39949(10) 0.0460(4) Uani d . 1 1
H H24 0.4468 0.9375 0.4356 0.055 Uiso calc R 1 1
C C25 0.45671(19) 0.96635(11) 0.32961(8) 0.0367(3) Uani d . 1 1
N N1 0.31385(16) 0.83887(9) 0.04768(7) 0.0369(3) Uani d . 1 1
N N2 0.27697(18) 0.96048(12) 0.31633(8) 0.0497(4) Uani d . 1 1
O O1 0.35888(18) 1.16282(9) 0.05773(7) 0.0589(4) Uani d . 1 1
H H1 0.3946 1.2066 0.0830 0.088 Uiso calc R 1 1
O O2 0.4894(3) 1.24286(10) 0.17434(9) 0.0816(5) Uani d . 1 1
O O3 0.26853(16) 0.67320(8) 0.01041(7) 0.0514(3) Uani d . 1 1
O O4 0.42270(13) 0.70889(8) 0.12536(6) 0.0419(3) Uani d . 1 1
O O5 0.20964(17) 1.00982(13) 0.27085(9) 0.0735(5) Uani d . 1 1
O O6 0.2029(2) 0.90511(16) 0.35160(11) 0.1023(7) Uani d . 1 1
F F1 0.74611(17) 0.94386(10) 0.48170(7) 0.0770(4) Uani d . 1 1
S S1 0.28971(5) 0.72821(3) 0.07403(2) 0.03511(11) Uani d . 1 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'
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'
F F 0.0171 0.0103 '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
C2 C1 C6 121.76(15)
C2 C1 N1 130.13(16)
C6 C1 N1 108.11(13)
C3 C2 C1 116.81(18)
C3 C2 H2 121.6
C1 C2 H2 121.6
C4 C3 C2 122.32(18)
C4 C3 H3 118.8
C2 C3 H3 118.8
C3 C4 C5 120.94(17)
C3 C4 H4 119.5
C5 C4 H4 119.5
C4 C5 C6 118.34(18)
C4 C5 H5 120.8
C6 C5 H5 120.8
C1 C6 C5 119.77(16)
C1 C6 C7 107.50(14)
C5 C6 C7 132.61(16)
C12 C7 C8 118.84(15)
C12 C7 C6 132.79(15)
C8 C7 C6 108.34(14)
C9 C8 C7 122.70(14)
C9 C8 N1 129.30(14)
C7 C8 N1 107.94(13)
C10 C9 C8 117.92(14)
C10 C9 H9 121.0
C8 C9 H9 121.0
C9 C10 C11 121.16(15)
C9 C10 C20 117.47(14)
C11 C10 C20 121.34(14)
C12 C11 C10 119.74(14)
C12 C11 C13 119.79(16)
C10 C11 C13 120.40(16)
O1 C12 C7 118.61(15)
O1 C12 C11 121.96(15)
C7 C12 C11 119.40(14)
O2 C13 C11 125.2(2)
O2 C13 H13 117.4
C11 C13 H13 117.4
C15 C14 C19 121.56(17)
C15 C14 S1 119.38(13)
C19 C14 S1 119.04(15)
C14 C15 C16 118.67(18)
C14 C15 H15 120.7
C16 C15 H15 120.7
C15 C16 C17 119.5(2)
C15 C16 H16 120.2
C17 C16 H16 120.2
C18 C17 C16 121.0(2)
C18 C17 H17 119.5
C16 C17 H17 119.5
C17 C18 C19 120.5(2)
C17 C18 H18 119.8
C19 C18 H18 119.8
C18 C19 C14 118.7(2)
C18 C19 H19 120.6
C14 C19 H19 120.6
C25 C20 C21 116.44(16)
C25 C20 C10 122.55(15)
C21 C20 C10 120.77(15)
C22 C21 C20 121.61(17)
C22 C21 H21 119.2
C20 C21 H21 119.2
C23 C22 C21 118.93(17)
C23 C22 H22 120.5
C21 C22 H22 120.5
F1 C23 C22 119.16(18)
F1 C23 C24 118.45(18)
C22 C23 C24 122.38(18)
C23 C24 C25 117.19(17)
C23 C24 H24 121.4
C25 C24 H24 121.4
C24 C25 C20 123.41(16)
C24 C25 N2 115.91(15)
C20 C25 N2 120.66(15)
C8 N1 C1 107.92(12)
C8 N1 S1 124.30(11)
C1 N1 S1 124.56(11)
O5 N2 O6 122.76(17)
O5 N2 C25 119.13(15)
O6 N2 C25 118.10(16)
C12 O1 H1 109.5
O3 S1 O4 119.96(7)
O3 S1 N1 106.50(7)
O4 S1 N1 106.35(7)
O3 S1 C14 109.70(8)
O4 S1 C14 108.93(8)
N1 S1 C14 104.19(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.384(2)
C1 C6 1.395(2)
C1 N1 1.427(2)
C2 C3 1.383(3)
C2 H2 0.9300
C3 C4 1.370(3)
C3 H3 0.9300
C4 C5 1.375(3)
C4 H4 0.9300
C5 C6 1.395(2)
C5 H5 0.9300
C6 C7 1.437(2)
C7 C12 1.390(2)
C7 C8 1.396(2)
C8 C9 1.390(2)
C8 N1 1.4117(19)
C9 C10 1.370(2)
C9 H9 0.9300
C10 C11 1.414(2)
C10 C20 1.490(2)
C11 C12 1.402(2)
C11 C13 1.437(2)
C12 O1 1.3411(19)
C13 O2 1.218(2)
C13 H13 0.9300
C14 C15 1.381(3)
C14 C19 1.384(2)
C14 S1 1.7459(18)
C15 C16 1.384(3)
C15 H15 0.9300
C16 C17 1.385(4)
C16 H16 0.9300
C17 C18 1.359(4)
C17 H17 0.9300
C18 C19 1.374(3)
C18 H18 0.9300
C19 H19 0.9300
C20 C25 1.387(2)
C20 C21 1.394(2)
C21 C22 1.373(3)
C21 H21 0.9300
C22 C23 1.368(3)
C22 H22 0.9300
C23 F1 1.345(2)
C23 C24 1.370(3)
C24 C25 1.375(2)
C24 H24 0.9300
C25 N2 1.467(2)
N1 S1 1.6608(14)
N2 O5 1.202(2)
N2 O6 1.209(2)
O1 H1 0.8200
O3 S1 1.4189(12)
O4 S1 1.4202(13)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O2 ----- 0.82 1.89 2.611(3) 146
C2 H2 O3 ----- 0.93 2.37 2.956(3) 121
C9 H9 O4 ----- 0.93 2.30 2.902(3) 122
C18 H18 O4 1_455 0.93 2.55 3.221(3) 129
C13 H13 O4 2_655 0.93 2.50 3.337(3) 150
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 -2.3(3)
N1 C1 C2 C3 177.26(16)
C1 C2 C3 C4 1.4(3)
C2 C3 C4 C5 0.8(3)
C3 C4 C5 C6 -1.9(3)
C2 C1 C6 C5 1.2(2)
N1 C1 C6 C5 -178.45(14)
C2 C1 C6 C7 177.77(15)
N1 C1 C6 C7 -1.89(17)
C4 C5 C6 C1 0.9(2)
C4 C5 C6 C7 -174.60(17)
C1 C6 C7 C12 -178.73(17)
C5 C6 C7 C12 -2.8(3)
C1 C6 C7 C8 -0.87(17)
C5 C6 C7 C8 175.08(16)
C12 C7 C8 C9 4.2(2)
C6 C7 C8 C9 -174.01(14)
C12 C7 C8 N1 -178.49(13)
C6 C7 C8 N1 3.30(16)
C7 C8 C9 C10 0.0(2)
N1 C8 C9 C10 -176.72(14)
C8 C9 C10 C11 -4.0(2)
C8 C9 C10 C20 173.94(14)
C9 C10 C11 C12 3.8(2)
C20 C10 C11 C12 -174.03(15)
C9 C10 C11 C13 -179.24(16)
C20 C10 C11 C13 2.9(2)
C8 C7 C12 O1 177.74(14)
C6 C7 C12 O1 -4.6(3)
C8 C7 C12 C11 -4.3(2)
C6 C7 C12 C11 173.39(16)
C10 C11 C12 O1 178.36(15)
C13 C11 C12 O1 1.4(3)
C10 C11 C12 C7 0.5(2)
C13 C11 C12 C7 -176.50(16)
C12 C11 C13 O2 -0.9(3)
C10 C11 C13 O2 -177.9(2)
C19 C14 C15 C16 -1.4(3)
S1 C14 C15 C16 176.77(14)
C14 C15 C16 C17 1.1(3)
C15 C16 C17 C18 0.1(3)
C16 C17 C18 C19 -1.0(4)
C17 C18 C19 C14 0.7(3)
C15 C14 C19 C18 0.5(3)
S1 C14 C19 C18 -177.66(16)
C9 C10 C20 C25 -75.8(2)
C11 C10 C20 C25 102.15(19)
C9 C10 C20 C21 98.30(19)
C11 C10 C20 C21 -83.8(2)
C25 C20 C21 C22 -0.4(3)
C10 C20 C21 C22 -174.86(17)
C20 C21 C22 C23 1.0(3)
C21 C22 C23 F1 179.39(18)
C21 C22 C23 C24 0.0(3)
F1 C23 C24 C25 179.14(16)
C22 C23 C24 C25 -1.4(3)
C23 C24 C25 C20 2.0(3)
C23 C24 C25 N2 -179.38(16)
C21 C20 C25 C24 -1.1(2)
C10 C20 C25 C24 173.19(16)
C21 C20 C25 N2 -179.64(15)
C10 C20 C25 N2 -5.3(2)
C9 C8 N1 C1 172.62(15)
C7 C8 N1 C1 -4.45(16)
C9 C8 N1 S1 12.2(2)
C7 C8 N1 S1 -164.88(11)
C2 C1 N1 C8 -175.68(16)
C6 C1 N1 C8 3.93(16)
C2 C1 N1 S1 -15.3(2)
C6 C1 N1 S1 164.29(11)
C24 C25 N2 O5 147.23(18)
C20 C25 N2 O5 -34.1(2)
C24 C25 N2 O6 -33.4(3)
C20 C25 N2 O6 145.2(2)
C8 N1 S1 O3 -165.23(12)
C1 N1 S1 O3 37.55(14)
C8 N1 S1 O4 -36.20(14)
C1 N1 S1 O4 166.58(12)
C8 N1 S1 C14 78.81(14)
C1 N1 S1 C14 -78.41(14)
C15 C14 S1 O3 166.60(13)
C19 C14 S1 O3 -15.16(16)
C15 C14 S1 O4 33.48(15)
C19 C14 S1 O4 -148.28(14)
C15 C14 S1 N1 -79.71(14)
C19 C14 S1 N1 98.53(14)
