#------------------------------------------------------------------------------
#$Date: 2015-09-26 05:24:55 +0300 (Sat, 26 Sep 2015) $
#$Revision: 158362 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241109.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_2241109
loop_
_publ_author_name
'Jotani, Mukesh M.'
'Gajera, Nilesh N.'
'Patel, Mukesh C.'
'Sung, Herman H. Y.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 A monoclinic polymorph of
 4-(2H-1,3-benzodioxol-5-yl)-1-(4-methylphenyl)-1H-pyrazol-5-amine
;
_journal_coeditor_code           HB7490
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1121
_journal_page_last               1124
_journal_paper_doi               10.1107/S2056989015016023
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C17 H15 N3 O2'
_chemical_formula_moiety         'C17 H15 N3 O2'
_chemical_formula_sum            'C17 H15 N3 O2'
_chemical_formula_weight         293.32
_chemical_name_systematic
4-(2H-1,3-Benzodioxol-5-yl)-1-(4-methylphenyl)-1H-pyrazol-5-amine
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 109.844(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9652(3)
_cell_length_b                   10.6898(2)
_cell_length_c                   9.8459(2)
_cell_measurement_reflns_used    2900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.64
_cell_measurement_theta_min      5.34
_cell_volume                     1382.57(5)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway,
2001) and
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXL97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4379
_diffrn_reflns_theta_full        69.952
_diffrn_reflns_theta_max         69.952
_diffrn_reflns_theta_min         5.335
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0527P)²+0.5203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                2289
_reflns_number_total             2582
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7490sup1.cif
_cod_data_source_block           I
_cod_database_code               2241109
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.774
_shelx_estimated_absorpt_t_max   0.893
loop_
_space_group_symop_operation_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_occupancy
O O1 -0.01538(7) 0.79537(9) 0.05812(10) 0.0229(2) Uani d 1
O O2 0.09248(7) 0.63677(9) 0.17958(10) 0.0229(2) Uani d 1
N N1 0.47346(8) 0.93081(10) 0.71284(11) 0.0146(2) Uani d 1
N N2 0.46867(8) 1.04737(10) 0.65038(11) 0.0168(2) Uani d 1
N N3 0.38155(8) 0.73744(11) 0.67648(13) 0.0229(3) Uani d 1
H H1N 0.4302(10) 0.6978(15) 0.7442(15) 0.028 Uiso d 1
H H2N 0.3203(8) 0.7054(15) 0.6459(17) 0.028 Uiso d 1
C C1 0.79815(10) 0.85389(13) 1.24901(15) 0.0226(3) Uani d 1
H H1A 0.7964 0.9221 1.3147 0.034 Uiso calc 1
H H1B 0.8637 0.8547 1.2330 0.034 Uiso calc 1
H H1C 0.7896 0.7737 1.2917 0.034 Uiso calc 1
C C2 0.71312(10) 0.87116(12) 1.10672(14) 0.0178(3) Uani d 1
C C3 0.73229(9) 0.91569(12) 0.98529(14) 0.0188(3) Uani d 1
H H3 0.8002 0.9347 0.9919 0.023 Uiso calc 1
C C4 0.65366(9) 0.93269(12) 0.85479(14) 0.0173(3) Uani d 1
H H4 0.6679 0.9627 0.7728 0.021 Uiso calc 1
C C5 0.55400(9) 0.90549(11) 0.84473(13) 0.0146(3) Uani d 1
C C6 0.53312(9) 0.86113(11) 0.96412(13) 0.0161(3) Uani d 1
H H6 0.4651 0.8427 0.9574 0.019 Uiso calc 1
C C7 0.61276(10) 0.84398(12) 1.09371(14) 0.0174(3) Uani d 1
H H7 0.5984 0.8130 1.1752 0.021 Uiso calc 1
C C8 0.39184(9) 0.85823(12) 0.63961(13) 0.0149(3) Uani d 1
C C9 0.33011(9) 0.93033(12) 0.52569(13) 0.0154(3) Uani d 1
C C10 0.38242(10) 1.04516(12) 0.54044(13) 0.0170(3) Uani d 1
H H10 0.3579 1.1141 0.4773 0.020 Uiso calc 1
C C11 0.23592(9) 0.89631(12) 0.40828(13) 0.0157(3) Uani d 1
C C12 0.16893(9) 0.99103(12) 0.33479(14) 0.0180(3) Uani d 1
H H12 0.1828 1.0747 0.3683 0.022 Uiso calc 1
C C13 0.08223(10) 0.96750(13) 0.21382(14) 0.0199(3) Uani d 1
H H13 0.0379 1.0328 0.1646 0.024 Uiso calc 1
C C14 0.06491(9) 0.84515(13) 0.17031(13) 0.0177(3) Uani d 1
C C15 0.12917(9) 0.75009(12) 0.24281(14) 0.0170(3) Uani d 1
C C16 0.21486(9) 0.77116(12) 0.36133(14) 0.0169(3) Uani d 1
H H16 0.2580 0.7044 0.4095 0.020 Uiso calc 1
C C17 0.01608(10) 0.66946(14) 0.04489(14) 0.0217(3) Uani d 1
H H17A -0.0427 0.6118 0.0237 0.026 Uiso calc 1
H H17B 0.0442 0.6637 -0.0347 0.026 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C15 O2 C17 104.43(10)
C14 O1 C17 104.05(9)
C8 N1 N2 111.85(10)
C8 N1 C5 129.22(11)
N2 N1 C5 118.74(10)
C10 N2 N1 104.01(10)
C8 N3 H1N 122.2(11)
C8 N3 H2N 117.3(11)
H1N N3 H2N 119.0(16)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C7 C2 C3 118.16(12)
C7 C2 C1 120.64(12)
C3 C2 C1 121.20(12)
C4 C3 C2 121.06(12)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 119.71(12)
C3 C4 H4 120.1
C5 C4 H4 120.1
C6 C5 C4 120.25(11)
C6 C5 N1 120.59(11)
C4 C5 N1 119.06(11)
C5 C6 C7 119.32(11)
C5 C6 H6 120.3
C7 C6 H6 120.3
C6 C7 C2 121.51(12)
C6 C7 H7 119.2
C2 C7 H7 119.2
N3 C8 N1 122.88(11)
N3 C8 C9 130.31(12)
N1 C8 C9 106.77(11)
C8 C9 C10 103.96(11)
C8 C9 C11 129.77(12)
C10 C9 C11 126.12(11)
N2 C10 C9 113.40(11)
N2 C10 H10 123.3
C9 C10 H10 123.3
C12 C11 C16 119.12(12)
C12 C11 C9 119.26(12)
C16 C11 C9 121.47(11)
C11 C12 C13 122.76(12)
C11 C12 H12 118.6
C13 C12 H12 118.6
C14 C13 C12 116.48(12)
C14 C13 H13 121.8
C12 C13 H13 121.8
C13 C14 C15 121.64(12)
C13 C14 O1 128.63(12)
C15 C14 O1 109.69(12)
C16 C15 O2 127.53(12)
C16 C15 C14 122.83(12)
O2 C15 C14 109.63(11)
C15 C16 C11 117.16(11)
C15 C16 H16 121.4
C11 C16 H16 121.4
O2 C17 O1 107.40(10)
O2 C17 H17A 110.2
O1 C17 H17A 110.2
O2 C17 H17B 110.2
O1 C17 H17B 110.2
H17A C17 H17B 108.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C15 1.3787(16)
O2 C17 1.4347(15)
O1 C14 1.3856(15)
O1 C17 1.4354(17)
N1 C8 1.3649(16)
N1 N2 1.3810(15)
N1 C5 1.4258(15)
N2 C10 1.3183(16)
N3 C8 1.3621(17)
N3 H1N 0.883(9)
N3 H2N 0.875(9)
C1 C2 1.5091(17)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C7 1.3940(19)
C2 C3 1.3946(19)
C3 C4 1.3898(17)
C3 H3 0.9500
C4 C5 1.3921(18)
C4 H4 0.9500
C5 C6 1.3872(18)
C6 C7 1.3911(17)
C6 H6 0.9500
C7 H7 0.9500
C8 C9 1.3925(17)
C9 C10 1.4105(17)
C9 C11 1.4719(17)
C10 H10 0.9500
C11 C12 1.4016(18)
C11 C16 1.4134(18)
C12 C13 1.4032(17)
C12 H12 0.9500
C13 C14 1.372(2)
C13 H13 0.9500
C14 C15 1.3830(18)
C15 C16 1.3771(17)
C16 H16 0.9500
C17 H17A 0.9900
C17 H17B 0.9900
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
N3 H1N N2 2_646 0.882(15) 2.159(15) 2.9981(16) 158.6(14)
C10 H10 Cg1 2_656 0.95 2.97 3.6753(14) 133
C17 H17B Cg2 4_564 0.99 2.66 3.6334(15) 169
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
C8 N1 N2 C10 1.15(13)
C5 N1 N2 C10 -174.21(10)
C7 C2 C3 C4 0.04(19)
C1 C2 C3 C4 -179.34(12)
C2 C3 C4 C5 0.3(2)
C3 C4 C5 C6 -0.26(19)
C3 C4 C5 N1 176.08(11)
C8 N1 C5 C6 -47.97(18)
N2 N1 C5 C6 126.47(12)
C8 N1 C5 C4 135.70(13)
N2 N1 C5 C4 -49.86(16)
C4 C5 C6 C7 -0.10(18)
N1 C5 C6 C7 -176.39(11)
C5 C6 C7 C2 0.44(19)
C3 C2 C7 C6 -0.41(19)
C1 C2 C7 C6 178.98(12)
N2 N1 C8 N3 177.01(11)
C5 N1 C8 N3 -8.2(2)
N2 N1 C8 C9 -0.87(14)
C5 N1 C8 C9 173.88(11)
N3 C8 C9 C10 -177.44(13)
N1 C8 C9 C10 0.23(13)
N3 C8 C9 C11 -1.7(2)
N1 C8 C9 C11 176.01(12)
N1 N2 C10 C9 -1.00(14)
C8 C9 C10 N2 0.51(14)
C11 C9 C10 N2 -175.48(11)
C8 C9 C11 C12 158.82(13)
C10 C9 C11 C12 -26.24(19)
C8 C9 C11 C16 -25.6(2)
C10 C9 C11 C16 149.34(13)
C16 C11 C12 C13 -1.36(19)
C9 C11 C12 C13 174.33(11)
C11 C12 C13 C14 0.57(19)
C12 C13 C14 C15 0.53(19)
C12 C13 C14 O1 178.07(12)
C17 O1 C14 C13 168.94(14)
C17 O1 C14 C15 -13.28(14)
C17 O2 C15 C16 -168.01(13)
C17 O2 C15 C14 13.12(14)
C13 C14 C15 C16 -0.8(2)
O1 C14 C15 C16 -178.81(11)
C13 C14 C15 O2 178.09(12)
O1 C14 C15 O2 0.12(15)
O2 C15 C16 C11 -178.70(12)
C14 C15 C16 C11 0.03(19)
C12 C11 C16 C15 1.02(18)
C9 C11 C16 C15 -174.57(11)
C15 O2 C17 O1 -21.31(13)
C14 O1 C17 O2 21.29(13)

_cod_database_fobs_code 2241109
