#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/81/7118111.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_7118111
loop_
_publ_author_name
'Sayani Mukherjee'
'P. S. Salini'
'A. Srinivasan'
'S Peruncheralathan'
_publ_section_title
;
 AIEE phenomenon: tetraaryl vs. triaryl pyrazoles
;
_journal_name_full               Chem.Commun.
_journal_page_first              17148
_journal_paper_doi               10.1039/C5cc05973A
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C21 H16 N2'
_chemical_formula_weight         296.36
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-10-31 deposited with the CCDC.
2015-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_formula_units_Z            16
_cell_length_a                   29.627(10)
_cell_length_b                   36.790(12)
_cell_length_c                   5.865(2)
_cell_measurement_reflns_used    4601
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.71
_cell_measurement_theta_min      2.21
_cell_volume                     6393(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT  A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            25733
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_process_details   SADABS-2008/1
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.016
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.008
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0401
_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)+(0.0552P)²+0.9593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                2867
_reflns_number_total             3652
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5cc05973a2.cif
_cod_data_source_block           preu_sm_tpp
_cod_original_cell_volume        6393(6)
_cod_original_sg_symbol_H-M      'Fdd2 '
_cod_database_code               7118111
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.37159(5) -0.04089(4) 0.2873(3) 0.0437(3) Uani 1 1 d . . .
C2 C 0.37384(6) -0.06954(4) 0.4415(3) 0.0560(4) Uani 1 1 d . . .
H2 H 0.3868 -0.0658 0.5839 0.067 Uiso 1 1 calc R . .
C3 C 0.35709(6) -0.10342(4) 0.3866(4) 0.0642(5) Uani 1 1 d . . .
H3 H 0.3593 -0.1224 0.4909 0.077 Uiso 1 1 calc R . .
C4 C 0.33733(6) -0.10917(4) 0.1794(4) 0.0599(5) Uani 1 1 d . . .
H4 H 0.3255 -0.1319 0.1436 0.072 Uiso 1 1 calc R . .
C5 C 0.33491(6) -0.08123(5) 0.0237(3) 0.0571(4) Uani 1 1 d . . .
H5 H 0.3217 -0.0852 -0.1179 0.068 Uiso 1 1 calc R . .
C6 C 0.35199(5) -0.04733(4) 0.0760(3) 0.0492(4) Uani 1 1 d . . .
H6 H 0.3504 -0.0287 -0.0309 0.059 Uiso 1 1 calc R . .
C7 C 0.33959(5) 0.03729(4) 0.1470(3) 0.0461(4) Uani 1 1 d . . .
C8 C 0.29737(6) 0.02968(5) 0.2322(4) 0.0667(5) Uani 1 1 d . . .
H8 H 0.2938 0.0182 0.3721 0.080 Uiso 1 1 calc R . .
C9 C 0.26029(7) 0.03985(7) 0.1014(6) 0.1007(10) Uani 1 1 d . . .
H9 H 0.2314 0.0350 0.1551 0.121 Uiso 1 1 calc R . .
C10 C 0.26545(13) 0.05664(7) -0.1025(7) 0.1226(13) Uani 1 1 d . . .
H10 H 0.2403 0.0635 -0.1868 0.147 Uiso 1 1 calc R . .
C11 C 0.30827(12) 0.06346(6) -0.1844(5) 0.1040(10) Uani 1 1 d . . .
H11 H 0.3118 0.0746 -0.3256 0.125 Uiso 1 1 calc R . .
C12 C 0.34558(8) 0.05401(5) -0.0605(3) 0.0669(5) Uani 1 1 d . . .
H12 H 0.3744 0.0588 -0.1154 0.080 Uiso 1 1 calc R . .
C13 C 0.46840(5) 0.05866(4) 0.6282(3) 0.0481(4) Uani 1 1 d . . .
C14 C 0.48220(5) 0.04624(5) 0.8407(3) 0.0569(4) Uani 1 1 d . . .
H14 H 0.4686 0.0258 0.9035 0.068 Uiso 1 1 calc R . .
C15 C 0.51594(7) 0.06388(6) 0.9598(4) 0.0714(6) Uani 1 1 d . . .
H15 H 0.5253 0.0550 1.1006 0.086 Uiso 1 1 calc R . .
C16 C 0.53555(7) 0.09437(6) 0.8708(4) 0.0764(6) Uani 1 1 d U . .
H16 H 0.5583 0.1062 0.9510 0.092 Uiso 1 1 calc R . .
C17 C 0.52167(6) 0.10768(5) 0.6620(4) 0.0734(6) Uani 1 1 d U . .
H17 H 0.5349 0.1286 0.6030 0.088 Uiso 1 1 calc R . .
C18 C 0.48814(5) 0.08995(4) 0.5403(3) 0.0577(4) Uani 1 1 d . . .
H18 H 0.4789 0.0990 0.3998 0.069 Uiso 1 1 calc R . .
N1 N 0.37852(4) 0.02757(3) 0.2778(2) 0.0465(3) Uani 1 1 d . . .
N2 N 0.40435(4) 0.05499(3) 0.3652(2) 0.0483(3) Uani 1 1 d . . .
C23 C 0.39144(5) -0.00577(4) 0.3557(3) 0.0432(3) Uani 1 1 d . . .
C24 C 0.42726(5) 0.00061(4) 0.4982(3) 0.0496(4) Uani 1 1 d . . .
H24 H 0.4438 -0.0167 0.5786 0.060 Uiso 1 1 calc R . .
C25 C 0.43402(5) 0.03816(4) 0.4988(3) 0.0457(4) Uani 1 1 d . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 C1 C2 118.11(14) . .
C6 C1 C23 123.95(14) . .
C2 C1 C23 117.92(15) . .
C3 C2 C1 121.06(17) . .
C3 C2 H2 119.5 . .
C1 C2 H2 119.5 . .
C4 C3 C2 120.12(17) . .
C4 C3 H3 119.9 . .
C2 C3 H3 119.9 . .
C3 C4 C5 119.80(16) . .
C3 C4 H4 120.1 . .
C5 C4 H4 120.1 . .
C4 C5 C6 120.53(17) . .
C4 C5 H5 119.7 . .
C6 C5 H5 119.7 . .
C5 C6 C1 120.37(16) . .
C5 C6 H6 119.8 . .
C1 C6 H6 119.8 . .
C12 C7 C8 121.98(17) . .
C12 C7 N1 118.84(16) . .
C8 C7 N1 119.18(17) . .
C7 C8 C9 117.6(2) . .
C7 C8 H8 121.2 . .
C9 C8 H8 121.2 . .
C10 C9 C8 121.3(3) . .
C10 C9 H9 119.3 . .
C8 C9 H9 119.3 . .
C9 C10 C11 119.6(2) . .
C9 C10 H10 120.2 . .
C11 C10 H10 120.2 . .
C12 C11 C10 120.8(3) . .
C12 C11 H11 119.6 . .
C10 C11 H11 119.6 . .
C11 C12 C7 118.7(2) . .
C11 C12 H12 120.7 . .
C7 C12 H12 120.7 . .
C14 C13 C18 118.77(15) . .
C14 C13 C25 119.75(15) . .
C18 C13 C25 121.46(16) . .
C15 C14 C13 120.82(18) . .
C15 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C16 C15 C14 120.0(2) . .
C16 C15 H15 120.0 . .
C14 C15 H15 120.0 . .
C15 C16 C17 120.19(18) . .
C15 C16 H16 119.9 . .
C17 C16 H16 119.9 . .
C16 C17 C18 120.2(2) . .
C16 C17 H17 119.9 . .
C18 C17 H17 119.9 . .
C17 C18 C13 120.0(2) . .
C17 C18 H18 120.0 . .
C13 C18 H18 120.0 . .
C23 N1 N2 112.40(12) . .
C23 N1 C7 129.10(12) . .
N2 N1 C7 117.94(11) . .
C25 N2 N1 104.33(12) . .
N1 C23 C24 105.53(12) . .
N1 C23 C1 125.79(13) . .
C24 C23 C1 128.61(13) . .
C23 C24 C25 106.37(13) . .
C23 C24 H24 126.8 . .
C25 C24 H24 126.8 . .
N2 C25 C24 111.37(13) . .
N2 C25 C13 121.37(13) . .
C24 C25 C13 127.25(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.389(2) .
C1 C2 1.390(2) .
C1 C23 1.475(2) .
C2 C3 1.380(2) .
C2 H2 0.9300 .
C3 C4 1.366(3) .
C3 H3 0.9300 .
C4 C5 1.377(3) .
C4 H4 0.9300 .
C5 C6 1.381(2) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C12 1.375(3) .
C7 C8 1.376(2) .
C7 N1 1.4303(19) .
C8 C9 1.391(3) .
C8 H8 0.9300 .
C9 C10 1.355(5) .
C9 H9 0.9300 .
C10 C11 1.379(5) .
C10 H10 0.9300 .
C11 C12 1.368(3) .
C11 H11 0.9300 .
C12 H12 0.9300 .
C13 C14 1.389(3) .
C13 C18 1.391(2) .
C13 C25 1.477(2) .
C14 C15 1.382(2) .
C14 H14 0.9300 .
C15 C16 1.367(3) .
C15 H15 0.9300 .
C16 C17 1.381(3) .
C16 H16 0.9300 .
C17 C18 1.387(2) .
C17 H17 0.9300 .
C18 H18 0.9300 .
N1 C23 1.3637(19) .
N1 N2 1.3660(16) .
N2 C25 1.330(2) .
C23 C24 1.371(2) .
C24 C25 1.396(2) .
C24 H24 0.9300 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 0.0(3) . . . .
C23 C1 C2 C3 -178.19(16) . . . .
C1 C2 C3 C4 -0.9(3) . . . .
C2 C3 C4 C5 1.2(3) . . . .
C3 C4 C5 C6 -0.6(3) . . . .
C4 C5 C6 C1 -0.4(2) . . . .
C2 C1 C6 C5 0.7(2) . . . .
C23 C1 C6 C5 178.74(15) . . . .
C12 C7 C8 C9 -0.6(3) . . . .
N1 C7 C8 C9 179.35(16) . . . .
C7 C8 C9 C10 0.0(3) . . . .
C8 C9 C10 C11 0.8(4) . . . .
C9 C10 C11 C12 -1.1(4) . . . .
C10 C11 C12 C7 0.5(3) . . . .
C8 C7 C12 C11 0.3(3) . . . .
N1 C7 C12 C11 -179.61(17) . . . .
C18 C13 C14 C15 -2.1(2) . . . .
C25 C13 C14 C15 176.67(14) . . . .
C13 C14 C15 C16 1.3(2) . . . .
C14 C15 C16 C17 0.2(3) . . . .
C15 C16 C17 C18 -0.8(3) . . . .
C16 C17 C18 C13 0.0(3) . . . .
C14 C13 C18 C17 1.4(2) . . . .
C25 C13 C18 C17 -177.27(14) . . . .
C12 C7 N1 C23 -121.82(18) . . . .
C8 C7 N1 C23 58.2(2) . . . .
C12 C7 N1 N2 67.5(2) . . . .
C8 C7 N1 N2 -112.49(17) . . . .
C23 N1 N2 C25 0.35(17) . . . .
C7 N1 N2 C25 172.58(14) . . . .
N2 N1 C23 C24 -0.29(18) . . . .
C7 N1 C23 C24 -171.43(16) . . . .
N2 N1 C23 C1 -177.53(14) . . . .
C7 N1 C23 C1 11.3(3) . . . .
C6 C1 C23 N1 28.8(2) . . . .
C2 C1 C23 N1 -153.12(16) . . . .
C6 C1 C23 C24 -147.77(17) . . . .
C2 C1 C23 C24 30.3(2) . . . .
N1 C23 C24 C25 0.11(18) . . . .
C1 C23 C24 C25 177.24(16) . . . .
N1 N2 C25 C24 -0.28(18) . . . .
N1 N2 C25 C13 -179.55(14) . . . .
C23 C24 C25 N2 0.11(19) . . . .
C23 C24 C25 C13 179.33(15) . . . .
C14 C13 C25 N2 146.46(15) . . . .
C18 C13 C25 N2 -34.8(2) . . . .
C14 C13 C25 C24 -32.7(2) . . . .
C18 C13 C25 C24 146.00(17) . . . .
