##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N-[7-Ethoxy-2-(prop-2-en-1-yl)-2H-indazol-6-yl]-4-
methylbenzenesulfonamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H21 N3 O3 S'
_chemical_formula_sum     'C19 H21 N3 O3 S'
_chemical_formula_iupac     'C19 H21 N3 O3 S'
_chemical_formula_weight     371.45
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_hall     '-P 2ybc'
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'
_cell_length_a     10.1459(7)
_cell_length_b     9.9506(7)
_cell_length_c     18.3720(13)
_cell_angle_alpha     90.00
_cell_angle_beta     95.097(3)
_cell_angle_gamma     90.00
_cell_volume     1847.5(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     243
_cell_measurement_theta_min     2.3
_cell_measurement_theta_max     27.2
_cell_measurement_temperature     296(2)
_cell_measurement_pressure     101
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.31
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.335
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     784
_exptl_absorpt_coefficient_mu     0.199
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD detector'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     20488
_diffrn_reflns_av_R_equivalents     0.0308
_diffrn_reflns_av_sigmaI/netI     0.0203
_diffrn_reflns_theta_min     2.02
_diffrn_reflns_theta_max     27.00
_diffrn_reflns_theta_full     27.00
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     4034
_reflns_number_gt     3693
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0391
_refine_ls_R_factor_gt     0.0358
_refine_ls_wR_factor_gt     0.0979
_refine_ls_wR_factor_ref     0.1001
_refine_ls_goodness_of_fit_ref     1.060
_refine_ls_restrained_S_all     1.060
_refine_ls_number_reflns     4034
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0522P)²+0.8814P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.688
_refine_diff_density_min     -0.392
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0206(15)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.76485(15) 0.66788(16) 0.17902(8) 0.0312(3) Uani d . 1 1 . .
    C C10 0.93118(13) 0.91852(15) -0.08185(7) 0.0252(3) Uani d . 1 1 . .
    C C11 0.79381(13) 0.94222(14) -0.07596(7) 0.0216(3) Uani d . 1 1 . .
    C C12 0.71089(12) 0.83505(13) -0.05612(7) 0.0207(3) Uani d . 1 1 . .
    C C13 0.98070(14) 1.04447(16) -0.09800(8) 0.0296(3) Uani d . 1 1 . .
    C C14 0.5674(2) 0.8996(2) 0.29302(10) 0.0556(6) Uani d . 1 1 . .
    C C15 0.50380(15) 0.94048(18) -0.09413(10) 0.0373(4) Uani d . 1 1 . .
    C C16 0.36049(15) 0.90887(17) -0.09383(10) 0.0354(4) Uani d . 1 1 . .
    C C17 0.88027(17) 1.27272(16) -0.11789(10) 0.0375(4) Uani d . 1 1 . .
    C C18 0.86633(18) 1.2985(2) -0.19860(12) 0.0523(5) Uani d . 1 1 . .
    C C19 0.8539(2) 1.2068(3) -0.24945(12) 0.0708(7) Uani d . 1 1 . .
    C C2 0.73094(17) 0.75204(19) 0.23458(9) 0.0389(4) Uani d . 1 1 . .
    C C3 0.60421(17) 0.80532(16) 0.23408(8) 0.0335(3) Uani d . 1 1 . .
    C C4 0.51129(15) 0.77163(14) 0.17715(8) 0.0283(3) Uani d . 1 1 . .
    C C5 0.54257(13) 0.68865(14) 0.12097(8) 0.0244(3) Uani d . 1 1 . .
    C C6 0.67012(13) 0.63684(13) 0.12255(7) 0.0211(3) Uani d . 1 1 . .
    C C7 0.76898(13) 0.71167(13) -0.04258(7) 0.0208(3) Uani d . 1 1 . .
    C C8 0.90547(13) 0.68843(14) -0.05067(8) 0.0256(3) Uani d . 1 1 . .
    C C9 0.98638(14) 0.78904(15) -0.06954(8) 0.0284(3) Uani d . 1 1 . .
    H H1 0.8499 0.6328 0.1797 0.037 Uiso calc R 1 1 . .
    H H13 1.0678 1.0651 -0.1057 0.036 Uiso calc R 1 1 . .
    H H14A 0.5216 0.9759 0.2711 0.083 Uiso calc R 1 1 . .
    H H14B 0.6461 0.9291 0.3214 0.083 Uiso calc R 1 1 . .
    H H14C 0.5109 0.8538 0.3242 0.083 Uiso calc R 1 1 . .
    H H15A 0.5298 0.9353 -0.1436 0.045 Uiso calc R 1 1 . .
    H H15B 0.5208 1.0310 -0.0761 0.045 Uiso calc R 1 1 . .
    H H16A 0.3429 0.8224 -0.1158 0.053 Uiso calc R 1 1 . .
    H H16B 0.3094 0.9761 -0.1211 0.053 Uiso calc R 1 1 . .
    H H16C 0.3368 0.9077 -0.0444 0.053 Uiso calc R 1 1 . .
    H H17A 0.9628 1.3116 -0.0969 0.045 Uiso calc R 1 1 . .
    H H17B 0.8085 1.3171 -0.0958 0.045 Uiso calc R 1 1 . .
    H H18 0.8666 1.3877 -0.2137 0.063 Uiso calc R 1 1 . .
    H H19A 0.8532 1.1163 -0.2367 0.085 Uiso calc R 1 1 . .
    H H19B 0.8458 1.2318 -0.2984 0.085 Uiso calc R 1 1 . .
    H H1N 0.6049 0.6137 -0.0394 0.026 Uiso d RD 1 1 . .
    H H2 0.7940 0.7731 0.2728 0.047 Uiso calc R 1 1 . .
    H H4 0.4259 0.8057 0.1768 0.034 Uiso calc R 1 1 . .
    H H5 0.4795 0.6678 0.0828 0.029 Uiso calc R 1 1 . .
    H H8 0.9400 0.6025 -0.0429 0.031 Uiso calc R 1 1 . .
    H H9 1.0756 0.7732 -0.0742 0.034 Uiso calc R 1 1 . .
    N N1 0.68677(11) 0.60110(11) -0.02548(6) 0.0216(2) Uani d D 1 1 . .
    N N2 0.76199(11) 1.07276(12) -0.08760(7) 0.0254(3) Uani d . 1 1 . .
    N N3 0.87862(12) 1.13021(12) -0.10026(7) 0.0275(3) Uani d . 1 1 . .
    O O1 0.57901(9) 0.84573(10) -0.04824(5) 0.0253(2) Uani d . 1 1 . .
    O O2 0.84526(10) 0.49024(11) 0.06679(6) 0.0292(2) Uani d . 1 1 . .
    O O3 0.61092(10) 0.41953(10) 0.04911(6) 0.0286(2) Uani d . 1 1 . .
    S S1 0.70831(3) 0.52451(3) 0.053468(17) 0.02072(11) Uani d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    C1 H1 . 0.9300 ?
    C1 C2 . 1.387(2) ?
    C10 C9 . 1.415(2) ?
    C10 C13 . 1.392(2) ?
    C11 C10 . 1.4271(18) ?
    C11 C12 . 1.4257(18) ?
    C11 N2 . 1.3509(18) ?
    C12 O1 . 1.3626(15) ?
    C13 H13 . 0.9300 ?
    C13 N3 . 1.340(2) ?
    C14 H14C . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14A . 0.9600 ?
    C15 H15B . 0.9700 ?
    C15 H15A . 0.9700 ?
    C15 C16 . 1.488(2) ?
    C15 O1 . 1.4380(17) ?
    C16 H16C . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16A . 0.9600 ?
    C17 H17B . 0.9700 ?
    C17 H17A . 0.9700 ?
    C17 C18 . 1.499(3) ?
    C17 N3 . 1.4549(19) ?
    C18 H18 . 0.9300 ?
    C19 H19B . 0.9300 ?
    C19 H19A . 0.9300 ?
    C19 C18 . 1.304(4) ?
    C2 H2 . 0.9300 ?
    C3 C14 . 1.505(2) ?
    C3 C2 . 1.390(2) ?
    C4 H4 . 0.9300 ?
    C4 C3 . 1.386(2) ?
    C5 H5 . 0.9300 ?
    C5 C4 . 1.381(2) ?
    C6 C5 . 1.3910(18) ?
    C6 C1 . 1.385(2) ?
    C7 N1 . 1.4323(17) ?
    C7 C8 . 1.4247(18) ?
    C7 C12 . 1.3749(18) ?
    C8 H8 . 0.9300 ?
    C8 C9 . 1.359(2) ?
    C9 H9 . 0.9300 ?
    N1 H1N . 0.8562 ?
    N2 N3 . 1.3528(16) ?
    S1 C6 . 1.7600(13) ?
    S1 N1 . 1.6358(11) ?
    S1 O3 . 1.4352(10) ?
    S1 O2 . 1.4305(10) ?
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
    C2 C1 H1 . . 120.5 ?
    C6 C1 H1 . . 120.5 ?
    C6 C1 C2 . . 119.01(14) ?
    C9 C10 C11 . . 120.91(13) ?
    C13 C10 C11 . . 103.93(12) ?
    C13 C10 C9 . . 135.12(13) ?
    C12 C11 C10 . . 119.89(12) ?
    N2 C11 C10 . . 111.60(12) ?
    N2 C11 C12 . . 128.43(12) ?
    C7 C12 C11 . . 117.44(12) ?
    O1 C12 C11 . . 125.18(12) ?
    O1 C12 C7 . . 117.36(12) ?
    C10 C13 H13 . . 126.6 ?
    N3 C13 H13 . . 126.6 ?
    N3 C13 C10 . . 106.70(12) ?
    H14B C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    C3 C14 H14C . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C3 C14 H14B . . 109.5 ?
    C3 C14 H14A . . 109.5 ?
    H15A C15 H15B . . 108.3 ?
    C16 C15 H15B . . 109.9 ?
    O1 C15 H15B . . 109.9 ?
    C16 C15 H15A . . 109.9 ?
    O1 C15 H15A . . 109.9 ?
    O1 C15 C16 . . 109.09(13) ?
    H16B C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    C15 C16 H16C . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C15 C16 H16B . . 109.5 ?
    C15 C16 H16A . . 109.5 ?
    H17A C17 H17B . . 107.8 ?
    C18 C17 H17B . . 109.1 ?
    N3 C17 H17B . . 109.1 ?
    C18 C17 H17A . . 109.1 ?
    N3 C17 H17A . . 109.1 ?
    N3 C17 C18 . . 112.65(15) ?
    C17 C18 H18 . . 117.2 ?
    C19 C18 H18 . . 117.2 ?
    C19 C18 C17 . . 125.68(19) ?
    H19A C19 H19B . . 120.0 ?
    C18 C19 H19B . . 120.0 ?
    C18 C19 H19A . . 120.0 ?
    C3 C2 H2 . . 119.5 ?
    C1 C2 H2 . . 119.5 ?
    C1 C2 C3 . . 121.00(14) ?
    C2 C3 C14 . . 121.45(16) ?
    C4 C3 C14 . . 119.87(15) ?
    C4 C3 C2 . . 118.67(14) ?
    C3 C4 H4 . . 119.2 ?
    C5 C4 H4 . . 119.2 ?
    C5 C4 C3 . . 121.52(13) ?
    C6 C5 H5 . . 120.6 ?
    C4 C5 H5 . . 120.6 ?
    C4 C5 C6 . . 118.77(13) ?
    C5 C6 S1 . . 118.97(10) ?
    C1 C6 S1 . . 119.95(11) ?
    C1 C6 C5 . . 121.02(13) ?
    C8 C7 N1 . . 119.24(12) ?
    C12 C7 N1 . . 118.49(11) ?
    C12 C7 C8 . . 122.08(12) ?
    C7 C8 H8 . . 119.3 ?
    C9 C8 H8 . . 119.3 ?
    C9 C8 C7 . . 121.45(13) ?
    C10 C9 H9 . . 120.9 ?
    C8 C9 H9 . . 120.9 ?
    C8 C9 C10 . . 118.16(12) ?
    S1 N1 H1N . . 112.5 ?
    C7 N1 H1N . . 112.9 ?
    C7 N1 S1 . . 121.19(9) ?
    C11 N2 N3 . . 103.48(11) ?
    N2 N3 C17 . . 118.53(12) ?
    C13 N3 C17 . . 127.12(13) ?
    C13 N3 N2 . . 114.27(12) ?
    C12 O1 C15 . . 117.63(11) ?
    N1 S1 C6 . . 108.84(6) ?
    O3 S1 C6 . . 107.93(6) ?
    O2 S1 C6 . . 107.50(6) ?
    O3 S1 N1 . . 104.63(6) ?
    O2 S1 N1 . . 108.30(6) ?
    O2 S1 O3 . . 119.30(6) ?
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
    N1 H1N O3 3_665 0.8600 2.2100 3.0199(15) 159.00 yes
    C8 H8 O2 3_765 0.9300 2.4400 3.1270(17) 131.00 yes
data_global
_journal_date_recd_electronic     2011-10-30
_journal_date_accepted     2011-10-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     12
_journal_page_first     o3211
_journal_page_last     o3211
_journal_paper_category     QO
_journal_coeditor_code     BT5700
_publ_contact_author_name     'El Mostapha Rakib'
_publ_contact_author_address
;
Laboratoire de Chimie Organique et Analytique,
Université Sultan Moulay Slimane, Faculté des Sciences et Techniques,
Béni-Mellal, BP 523,
Morocco
;
_publ_contact_author_email     'elmostapha1@ymail.com'
_publ_contact_author_fax     '00 212 555 444'
_publ_contact_author_phone     '00 212 66 66 66'
_publ_section_title
;\
N-[7-Ethoxy-2-(prop-2-en-1-yl)-2H-indazol-6-yl]-4-\
methylbenzenesulfonamide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Abbassi, Najat' .
;
Laboratoire de Chimie Organique et Analytique
Université Sultan Moulay Slimane,
Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco
;
    'Rakib, El Mostapha' .
;
Laboratoire de Chimie Organique et Analytique
Université Sultan Moulay Slimane,
Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco
;
    'Hannioui, Abdellah' .
;
Laboratoire de Chimie Organique et Analytique
Université Sultan Moulay Slimane,
Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco
;
    'Zouihri, Hafid' .
;
Laboratoires de Diffraction des Rayons X,
Centre Nationale pour la Recherche Scientifique et Technique, Rabat, Morocco
;
