#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/25/2222507.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_2222507
loop_
_publ_author_name
'Hökelek, Tuncer'
'Dal, Hakan'
'Tercan, Barış'
'Gülle, Sibel'
'Ergün, Yavuz'
_publ_section_title
;
 Ethyl 4-hydroxy-9-tosyl-9H-carbazole-3-carboxylate
;
_journal_coeditor_code           XU2536
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1515
_journal_page_last               o1516
_journal_paper_doi               10.1107/S1600536809021035
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H19 N O5 S'
_chemical_formula_moiety         'C22 H19 N O5 S'
_chemical_formula_sum            'C22 H19 N O5 S'
_chemical_formula_weight         409.44
_chemical_name_systematic
;
Ethyl 4-hydroxy-9-tosyl-9H-carbazole-3-carboxylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 119.6560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   23.2155(12)
_cell_length_b                   12.3581(7)
_cell_length_c                   15.1001(8)
_cell_measurement_reflns_used    4061
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.77
_cell_volume                     3764.7(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15402
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.93
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.467
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0377
_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)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                3276
_reflns_number_total             4658
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2536.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2222507
_cod_database_fobs_code          2222507
loop_
_symmetry_equiv_pos_as_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
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.212099(19) 0.58317(3) 0.16682(3) 0.01509(11) Uani d . 1 . .
O O1 -0.06829(6) 0.61107(10) 0.11936(9) 0.0201(3) Uani d . 1 . .
H H1A -0.0974(11) 0.5606(17) 0.1153(16) 0.048(7) Uiso d . 1 . .
O O2 0.23596(5) 0.66022(9) 0.12235(8) 0.0199(3) Uani d . 1 . .
O O3 0.21467(5) 0.47046(9) 0.14899(9) 0.0195(3) Uani d . 1 . .
O O4 -0.12557(5) 0.43127(10) 0.11530(9) 0.0208(3) Uani d . 1 . .
O O5 -0.07141(5) 0.27539(9) 0.13393(9) 0.0193(3) Uani d . 1 . .
C C1 0.08618(8) 0.42675(13) 0.13014(12) 0.0144(3) Uani d . 1 . .
H H1 0.1207(8) 0.3866(13) 0.1312(12) 0.018(4) Uiso d . 1 . .
C C2 0.03301(8) 0.37694(14) 0.12958(12) 0.0149(3) Uani d . 1 . .
H H2 0.0310(8) 0.2986(14) 0.1300(13) 0.018(5) Uiso d . 1 . .
C C3 -0.01988(7) 0.43566(13) 0.12663(11) 0.0141(3) Uani d . 1 . .
C C4 -0.01892(7) 0.54881(14) 0.12407(11) 0.0149(3) Uani d . 1 . .
C C4A 0.03495(7) 0.60124(13) 0.12560(11) 0.0138(3) Uani d . 1 . .
C C5 0.01396(8) 0.80917(14) 0.11276(13) 0.0193(4) Uani d . 1 . .
H H5 -0.0270(9) 0.8081(15) 0.1138(14) 0.027(5) Uiso d . 1 . .
C C5A 0.04860(8) 0.71408(13) 0.12014(12) 0.0150(3) Uani d . 1 . .
C C6 0.04061(9) 0.90650(14) 0.10672(13) 0.0230(4) Uani d . 1 . .
H H6 0.0177(8) 0.9736(14) 0.1024(12) 0.016(4) Uiso d . 1 . .
C C7 0.10079(9) 0.91078(15) 0.10819(14) 0.0233(4) Uani d . 1 . .
H H7 0.1175(9) 0.9779(15) 0.1057(14) 0.031(5) Uiso d . 1 . .
C C8 0.13612(9) 0.81785(14) 0.11499(13) 0.0198(4) Uani d . 1 . .
H H8 0.1773(9) 0.8231(14) 0.1173(14) 0.029(5) Uiso d . 1 . .
C C8A 0.10910(8) 0.71993(13) 0.12027(12) 0.0156(3) Uani d . 1 . .
C C9A 0.08633(7) 0.53939(13) 0.12851(11) 0.0135(3) Uani d . 1 . .
N N9 0.13218(6) 0.61218(10) 0.12305(10) 0.0141(3) Uani d . 1 . .
C C10 0.25002(7) 0.60690(13) 0.29814(12) 0.0142(3) Uani d . 1 . .
C C11 0.28921(8) 0.69829(13) 0.33915(13) 0.0183(4) Uani d . 1 . .
H H11 0.2962 0.7460 0.2977 0.022 Uiso calc R 1 . .
C C12 0.31773(8) 0.71715(14) 0.44291(13) 0.0193(4) Uani d . 1 . .
H H12 0.3448 0.7773 0.4711 0.023 Uiso calc R 1 . .
C C13 0.30678(8) 0.64815(13) 0.50581(12) 0.0161(4) Uani d . 1 . .
C C14 0.26657(8) 0.55758(13) 0.46226(13) 0.0175(4) Uani d . 1 . .
H H14 0.2585 0.5109 0.5032 0.021 Uiso calc R 1 . .
C C15 0.23858(8) 0.53610(13) 0.35925(12) 0.0171(3) Uani d . 1 . .
H H15 0.2124 0.4750 0.3312 0.020 Uiso calc R 1 . .
C C16 0.33734(8) 0.67164(14) 0.61810(12) 0.0203(4) Uani d . 1 . .
H H16A 0.3125 0.6354 0.6446 0.030 Uiso calc R 1 . .
H H16B 0.3367 0.7482 0.6282 0.030 Uiso calc R 1 . .
H H16C 0.3823 0.6463 0.6530 0.030 Uiso calc R 1 . .
C C17 -0.07694(8) 0.38237(14) 0.12438(12) 0.0160(3) Uani d . 1 . .
C C18 -0.12612(8) 0.21883(14) 0.13567(14) 0.0220(4) Uani d . 1 . .
H H18A -0.1649 0.2181 0.0682 0.026 Uiso calc R 1 . .
H H18B -0.1376 0.2543 0.1821 0.026 Uiso calc R 1 . .
C C19 -0.10271(10) 0.10619(15) 0.17057(17) 0.0345(5) Uani d . 1 . .
H H19A -0.1368 0.0664 0.1747 0.052 Uiso calc R 1 . .
H H1B -0.0636 0.1083 0.2365 0.052 Uiso calc R 1 . .
H H19C -0.0927 0.0715 0.1230 0.052 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 N9 . . 106.52(7) ?
O2 S1 C10 . . 109.07(7) ?
O3 S1 O2 . . 120.09(7) ?
O3 S1 N9 . . 106.08(7) ?
O3 S1 C10 . . 109.45(7) ?
N9 S1 C10 . . 104.46(7) ?
C4 O1 H1A . . 101.4(14) ?
C17 O5 C18 . . 116.08(13) ?
C2 C1 C9A . . 117.22(15) ?
C2 C1 H1 . . 121.4(10) ?
C9A C1 H1 . . 121.4(10) ?
C1 C2 C3 . . 122.37(16) ?
C1 C2 H2 . . 119.6(10) ?
C3 C2 H2 . . 118.1(10) ?
C2 C3 C17 . . 122.25(15) ?
C4 C3 C2 . . 119.37(15) ?
C4 C3 C17 . . 118.37(14) ?
O1 C4 C3 . . 123.04(14) ?
O1 C4 C4A . . 117.70(15) ?
C4A C4 C3 . . 119.26(14) ?
C4 C4A C5A . . 131.87(15) ?
C4 C4A C9A . . 119.28(15) ?
C9A C4A C5A . . 108.78(14) ?
C5A C5 H5 . . 121.5(11) ?
C6 C5 C5A . . 118.72(16) ?
C6 C5 H5 . . 119.7(11) ?
C5 C5A C4A . . 133.16(15) ?
C5 C5A C8A . . 119.49(15) ?
C8A C5A C4A . . 107.32(14) ?
C5 C6 C7 . . 120.98(17) ?
C5 C6 H6 . . 120.1(9) ?
C7 C6 H6 . . 118.9(9) ?
C6 C7 H7 . . 118.2(12) ?
C8 C7 C6 . . 121.62(17) ?
C8 C7 H7 . . 120.2(12) ?
C7 C8 H8 . . 119.9(11) ?
C8A C8 C7 . . 117.43(16) ?
C8A C8 H8 . . 122.6(11) ?
C5A C8A N9 . . 108.19(13) ?
C8 C8A C5A . . 121.76(15) ?
C8 C8A N9 . . 130.01(15) ?
C1 C9A N9 . . 129.78(14) ?
C1 C9A C4A . . 122.49(14) ?
C4A C9A N9 . . 107.62(14) ?
C8A N9 S1 . . 122.58(10) ?
C9A N9 S1 . . 123.76(11) ?
C9A N9 C8A . . 108.04(12) ?
C11 C10 S1 . . 119.51(12) ?
C11 C10 C15 . . 120.95(15) ?
C15 C10 S1 . . 119.51(12) ?
C10 C11 H11 . . 120.6 ?
C12 C11 C10 . . 118.81(15) ?
C12 C11 H11 . . 120.6 ?
C11 C12 C13 . . 121.51(15) ?
C11 C12 H12 . . 119.2 ?
C13 C12 H12 . . 119.2 ?
C12 C13 C14 . . 118.40(15) ?
C12 C13 C16 . . 120.46(15) ?
C14 C13 C16 . . 121.14(14) ?
C13 C14 H14 . . 119.5 ?
C15 C14 C13 . . 121.08(15) ?
C15 C14 H14 . . 119.5 ?
C10 C15 H15 . . 120.4 ?
C14 C15 C10 . . 119.24(15) ?
C14 C15 H15 . . 120.4 ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O4 C17 O5 . . 122.42(15) ?
O4 C17 C3 . . 123.56(16) ?
O5 C17 C3 . . 114.02(14) ?
O5 C18 C19 . . 106.54(14) ?
O5 C18 H18A . . 110.4 ?
O5 C18 H18B . . 110.4 ?
C19 C18 H18A . . 110.4 ?
C19 C18 H18B . . 110.4 ?
H18A C18 H18B . . 108.6 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H1B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H1B . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H1B C19 H19C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . 1.4257(11) ?
S1 O3 . 1.4255(12) ?
S1 N9 . 1.6715(13) ?
S1 C10 . 1.7508(16) ?
O1 C4 . 1.3527(18) ?
O1 H1A . 0.90(2) ?
O4 C17 . 1.2269(18) ?
O5 C17 . 1.3293(19) ?
O5 C18 . 1.4613(19) ?
C1 C2 . 1.376(2) ?
C1 H1 . 0.937(16) ?
C2 H2 . 0.970(17) ?
C3 C2 . 1.408(2) ?
C3 C4 . 1.399(2) ?
C3 C17 . 1.465(2) ?
C4A C4 . 1.398(2) ?
C4A C9A . 1.399(2) ?
C4A C5A . 1.441(2) ?
C5 H5 . 0.959(17) ?
C5A C5 . 1.397(2) ?
C5A C8A . 1.405(2) ?
C6 C5 . 1.376(2) ?
C6 C7 . 1.387(2) ?
C6 H6 . 0.970(17) ?
C7 H7 . 0.925(19) ?
C8 C7 . 1.385(2) ?
C8 H8 . 0.942(18) ?
C8A C8 . 1.383(2) ?
C9A C1 . 1.392(2) ?
N9 C9A . 1.4268(19) ?
N9 C8A . 1.428(2) ?
C10 C11 . 1.389(2) ?
C10 C15 . 1.389(2) ?
C11 H11 . 0.9300 ?
C12 C11 . 1.386(2) ?
C12 C13 . 1.390(2) ?
C12 H12 . 0.9300 ?
C14 C13 . 1.396(2) ?
C14 H14 . 0.9300 ?
C15 C14 . 1.383(2) ?
C15 H15 . 0.9300 ?
C16 C13 . 1.507(2) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C18 C19 . 1.492(2) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 H19A . 0.9600 ?
C19 H1B . 0.9600 ?
C19 H19C . 0.9600 ?
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
_geom_hbond_publ_flag
O1 H1A O4 . 0.90(3) 1.73(2) 2.5746(18) 156(2) yes
C12 H12 O1 8_566 0.93 2.55 3.410(2) 154 yes
C16 H16B Cg4 7_566 0.96 2.91 3.559(2) 126 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S1 N9 C8A . . . . -45.91(13) ?
O2 S1 N9 C9A . . . . 163.72(12) ?
O3 S1 N9 C8A . . . . -174.93(11) ?
O3 S1 N9 C9A . . . . 34.70(14) ?
C10 S1 N9 C8A . . . . 69.46(13) ?
C10 S1 N9 C9A . . . . -80.91(13) ?
O2 S1 C10 C11 . . . . 7.52(15) ?
O2 S1 C10 C15 . . . . -174.74(12) ?
O3 S1 C10 C11 . . . . 140.73(13) ?
O3 S1 C10 C15 . . . . -41.54(14) ?
N9 S1 C10 C11 . . . . -106.05(13) ?
N9 S1 C10 C15 . . . . 71.69(14) ?
C18 O5 C17 O4 . . . . -1.5(2) ?
C18 O5 C17 C3 . . . . 177.97(13) ?
C17 O5 C18 C19 . . . . -167.19(14) ?
C9A C1 C2 C3 . . . . 0.5(2) ?
C4 C3 C2 C1 . . . . 0.1(2) ?
C17 C3 C2 C1 . . . . 179.00(15) ?
C2 C3 C4 O1 . . . . 178.80(14) ?
C2 C3 C4 C4A . . . . -0.7(2) ?
C17 C3 C4 O1 . . . . -0.2(2) ?
C17 C3 C4 C4A . . . . -179.66(14) ?
C2 C3 C17 O4 . . . . -175.21(15) ?
C2 C3 C17 O5 . . . . 5.3(2) ?
C4 C3 C17 O4 . . . . 3.7(2) ?
C4 C3 C17 O5 . . . . -175.75(13) ?
C9A C4A C4 O1 . . . . -178.80(14) ?
C5A C4A C4 O1 . . . . -2.0(3) ?
C9A C4A C4 C3 . . . . 0.7(2) ?
C5A C4A C4 C3 . . . . 177.46(16) ?
C4 C4A C5A C5 . . . . 0.9(3) ?
C4 C4A C5A C8A . . . . -177.30(16) ?
C9A C4A C5A C5 . . . . 177.91(17) ?
C9A C4A C5A C8A . . . . -0.28(17) ?
C4 C4A C9A C1 . . . . -0.1(2) ?
C5A C4A C9A C1 . . . . -177.57(14) ?
C4 C4A C9A N9 . . . . 176.41(13) ?
C5A C4A C9A N9 . . . . -1.04(17) ?
C4A C5A C5 C6 . . . . -178.59(16) ?
C8A C5A C5 C6 . . . . -0.6(2) ?
C5 C5A C8A C8 . . . . 1.1(2) ?
C4A C5A C8A C8 . . . . 179.59(14) ?
C5 C5A C8A N9 . . . . -176.99(14) ?
C4A C5A C8A N9 . . . . 1.49(17) ?
C7 C6 C5 C5A . . . . -0.2(3) ?
C5 C6 C7 C8 . . . . 0.5(3) ?
C8A C8 C7 C6 . . . . 0.0(3) ?
N9 C8A C8 C7 . . . . 176.83(15) ?
C5A C8A C8 C7 . . . . -0.8(2) ?
N9 C9A C1 C2 . . . . -176.19(15) ?
C4A C9A C1 C2 . . . . -0.5(2) ?
S1 N9 C8A C5A . . . . -156.54(11) ?
S1 N9 C8A C8 . . . . 25.6(2) ?
C9A N9 C8A C5A . . . . -2.15(16) ?
C9A N9 C8A C8 . . . . 179.97(16) ?
S1 N9 C9A C1 . . . . -27.8(2) ?
S1 N9 C9A C4A . . . . 155.97(11) ?
C8A N9 C9A C1 . . . . 178.15(15) ?
C8A N9 C9A C4A . . . . 1.96(16) ?
S1 C10 C15 C14 . . . . -177.47(12) ?
C11 C10 C15 C14 . . . . 0.2(2) ?
S1 C10 C11 C12 . . . . 178.63(12) ?
C15 C10 C11 C12 . . . . 0.9(2) ?
C13 C12 C11 C10 . . . . -1.4(3) ?
C11 C12 C13 C14 . . . . 0.7(2) ?
C11 C12 C13 C16 . . . . -178.83(15) ?
C15 C14 C13 C12 . . . . 0.5(2) ?
C15 C14 C13 C16 . . . . -179.98(15) ?
C10 C15 C14 C13 . . . . -1.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742545
