#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/01/2200172.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_2200172
loop_
_publ_author_name
'Kubicki, Maciej'
'Codding, Penelope W.'
_publ_section_title
;1-(2-Pyridyl)-8H-pyrrolo[2,1-c]-s-triazolo[4,3-a][1,4]benzodiazepinium
 chloride
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o122
_journal_page_last               o124
_journal_paper_doi               10.1107/S1600536801000952
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C18 H14 N5 1+, Cl 1-'
_chemical_formula_moiety         'C18 H14 N5 1+, Cl 1-'
_chemical_formula_sum            'C18 H14 Cl N5'
_chemical_formula_weight         335.79
_chemical_name_systematic
;
1-(2-Pyridyl)-8H-pyrrolo[2,1-c]-s-triazolo[4,3-a][1,4]benzodiazepinium
chloride
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.513(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7856(5)
_cell_length_b                   8.2058(5)
_cell_length_c                   22.990(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      5
_cell_volume                     1649.7(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'ENPROC (Rettig, 1978)'
_computing_molecular_graphics
;
Stereochemical Workstation (Siemens, 1989)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
;
Stereochemical Workstation (Siemens, 1989)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .997
_diffrn_measured_fraction_theta_max .997
_diffrn_measurement_device_type  'CAD-4F four-circle'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  Ni-filter
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .048
_diffrn_reflns_av_sigmaI/netI    .0427
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            3604
_diffrn_reflns_theta_full        74.84
_diffrn_reflns_theta_max         74.84
_diffrn_reflns_theta_min         5.06
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  33
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .15
_refine_diff_density_max         .424
_refine_diff_density_min         -.546
_refine_ls_extinction_coef       .0098(6)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.257
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.257
_refine_ls_R_factor_all          .048
_refine_ls_R_factor_gt           .048
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.01P)²+0.70P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .113
_reflns_number_gt                3315
_reflns_number_total             3380
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na6035.cif
_cod_data_source_block           I
_cod_original_cell_volume        1649.8(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2200172
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_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
_atom_site_type_symbol
Cl1 .57862(5) .82294(7) .166179(19) .05235(18) Uani d . 1 . . Cl
C1 -.0478(2) .5787(2) .15720(8) .0428(4) Uani d . 1 . . C
H1 -.158(3) .587(3) .1477(10) .056(6) Uiso d . 1 . . H
C2 .0678(2) .5067(2) .13014(8) .0471(4) Uani d . 1 . . C
H2 .057(3) .455(3) .0961(10) .057(6) Uiso d . 1 . . H
C3 .2052(2) .5325(2) .16482(8) .0428(4) Uani d . 1 . . C
H3 .304(2) .494(3) .1596(9) .046(6) Uiso d . 1 . . H
C4 .16905(19) .6198(2) .21296(7) .0359(4) Uani d . 1 . . C
C5 .26225(19) .6754(2) .26350(7) .0354(4) Uani d . 1 . . C
N6 .40341(17) .7306(2) .26449(7) .0424(4) Uani d . 1 . . N
H6 .459(3) .759(3) .2313(10) .054(6) Uiso d . 1 . . H
N7 .46255(18) .7704(2) .31949(7) .0459(4) Uani d . 1 . . N
C8 .3530(2) .7391(2) .35263(8) .0393(4) Uani d . 1 . . C
N1' .2539(2) .8371(2) .43927(7) .0546(4) Uani d . 1 . . N
C2' .3703(2) .7668(2) .41603(8) .0419(4) Uani d . 1 . . C
C3' .5043(3) .7222(3) .44829(10) .0607(6) Uani d . 1 . . C
H3' .584(3) .672(3) .4275(12) .071(8) Uiso d . 1 . . H
C4' .5173(3) .7502(4) .50771(11) .0715(7) Uani d . 1 . . C
H4' .615(4) .730(4) .5307(14) .096(10) Uiso d . 1 . . H
C5' .3987(3) .8224(3) .53224(10) .0648(6) Uani d . 1 . . C
H5' .408(3) .843(3) .5744(12) .073(8) Uiso d . 1 . . H
C6' .2716(3) .8627(4) .49654(10) .0654(6) Uani d . 1 . . C
H6' .191(3) .908(4) .5103(12) .077(8) Uiso d . 1 . . H
N9 .22472(15) .68080(17) .31946(6) .0340(3) Uani d . 1 . . N
C10 .08906(19) .6093(2) .33966(7) .0350(4) Uani d . 1 . . C
C11 .1031(2) .5132(2) .38937(8) .0440(4) Uani d . 1 . . C
H11 .201(3) .497(3) .4101(9) .050(6) Uiso d . 1 . . H
C12 -.0272(3) .4441(3) .40865(10) .0543(5) Uani d . 1 . . C
H12 -.020(3) .383(4) .4469(13) .081(8) Uiso d . 1 . . H
C13 -.1677(3) .4676(3) .37776(10) .0560(5) Uani d . 1 . . C
H13 -.256(3) .417(4) .3920(11) .073(8) Uiso d . 1 . . H
C14 -.1796(2) .5601(3) .32752(10) .0487(5) Uani d . 1 . . C
H14 -.279(3) .573(3) .3040(10) .057(6) Uiso d . 1 . . H
C15 -.05162(19) .6339(2) .30754(8) .0378(4) Uani d . 1 . . C
C16 -.0641(2) .7316(2) .25220(8) .0405(4) Uani d . 1 . . C
H16B -.169(3) .744(3) .2376(10) .053(6) Uiso d . 1 . . H
H16A -.015(2) .840(3) .2590(9) .043(5) Uiso d . 1 . . H
N17 .01414(16) .64735(17) .20759(6) .0369(3) Uani d . 1 . . N
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .3639 .7018 '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
N17 C1 C2 108.2(2)
N17 C1 H1 118.0(10)
C2 C1 H1 134.0(10)
C1 C2 C3 108.2(2)
C1 C2 H2 126(2)
C3 C2 H2 126(2)
C4 C3 C2 106.4(2)
C4 C3 H3 124.0(10)
C2 C3 H3 129.0(10)
N17 C4 C3 108.4(2)
N17 C4 C5 120.4(2)
C3 C4 C5 131.2(2)
N6 C5 N9 106.6(2)
N6 C5 C4 126.0(2)
N9 C5 C4 127.4(2)
C5 N6 N7 111.90(10)
C5 N6 H6 128.0(10)
N7 N6 H6 120.0(10)
C8 N7 N6 104.9(2)
N7 C8 N9 110.6(2)
N7 C8 C2' 122.4(2)
N9 C8 C2' 127.0(2)
C6' N1' C2' 116.5(2)
N1' C2' C3' 123.3(2)
N1' C2' C8 117.1(2)
C3' C2' C8 119.6(2)
C4' C3' C2' 118.3(2)
C4' C3' H3' 124(2)
C2' C3' H3' 118(2)
C5' C4' C3' 119.1(2)
C5' C4' H4' 121(2)
C3' C4' H4' 120(2)
C6' C5' C4' 118.1(2)
C6' C5' H5' 123(2)
C4' C5' H5' 119(2)
N1' C6' C5' 124.8(3)
N1' C6' H6' 114(2)
C5' C6' H6' 122(2)
C5 N9 C8 105.90(10)
C5 N9 C10 125.00(10)
C8 N9 C10 128.10(10)
C11 C10 C15 121.7(2)
C11 C10 N9 119.1(2)
C15 C10 N9 119.2(2)
C10 C11 C12 119.0(2)
C10 C11 H11 120.0(10)
C12 C11 H11 121.0(10)
C13 C12 C11 120.3(2)
C13 C12 H12 120(2)
C11 C12 H12 120(2)
C12 C13 C14 120.1(2)
C12 C13 H13 119(2)
C14 C13 H13 121(2)
C13 C14 C15 121.1(2)
C13 C14 H14 121.0(10)
C15 C14 H14 118.0(10)
C10 C15 C14 117.7(2)
C10 C15 C16 121.1(2)
C14 C15 C16 121.1(2)
N17 C16 C15 110.00(10)
N17 C16 H16B 108.0(10)
C15 C16 H16B 110.0(10)
N17 C16 H16A 108.0(10)
C15 C16 H16A 111.0(10)
H16B C16 H16A 110(2)
C1 N17 C4 108.8(2)
C1 N17 C16 128.3(2)
C4 N17 C16 122.9(2)
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 N17 . 1.354(2) ?
C1 C2 . 1.374(3) ?
C1 H1 . .97(2) ?
C2 C3 . 1.398(3) ?
C2 H2 . .89(2) ?
C3 C4 . 1.381(2) ?
C3 H3 . .94(2) ?
C4 N17 . 1.373(2) ?
C4 C5 . 1.430(2) ?
C5 N6 . 1.319(2) ?
C5 N9 . 1.359(2) ?
N6 N7 . 1.360(2) ?
N6 H6 . .97(2) ?
N7 C8 . 1.309(2) ?
C8 N9 . 1.384(2) ?
C8 C2' . 1.469(2) ?
N1' C6' . 1.328(3) ?
N1' C2' . 1.330(3) ?
C2' C3' . 1.379(3) ?
C3' C4' . 1.379(3) ?
C3' H3' . .98(3) ?
C4' C5' . 1.367(4) ?
C4' H4' . .98(3) ?
C5' C6' . 1.362(4) ?
C5' H5' . .98(3) ?
C6' H6' . .88(3) ?
N9 C10 . 1.445(2) ?
C10 C11 . 1.384(2) ?
C10 C15 . 1.392(2) ?
C11 C12 . 1.388(3) ?
C11 H11 . .95(2) ?
C12 C13 . 1.377(3) ?
C12 H12 . 1.01(3) ?
C13 C14 . 1.378(3) ?
C13 H13 . .97(3) ?
C14 C15 . 1.394(3) ?
C14 H14 . .98(2) ?
C15 C16 . 1.499(3) ?
C16 N17 . 1.463(2) ?
C16 H16B . .95(2) ?
C16 H16A . .99(2) ?
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
N6 H6 Cl1 . .97(2) 1.98(2) 2.953(2) 177(2)
C16 H16B Cl1 1_455 .95(2) 2.71(2) 3.624(2) 161(2)
C5' H5' Cl1 4_576 .98(3) 2.82(3) 3.531(2) 130(2)
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
N17 C1 C2 C3 -.3(2)
C1 C2 C3 C4 .4(2)
C2 C3 C4 N17 -.4(2)
C2 C3 C4 C5 177.6(2)
N17 C4 C5 N6 -144.8(2)
C3 C4 C5 N6 37.4(3)
N17 C4 C5 N9 35.8(3)
C3 C4 C5 N9 -142.0(2)
N9 C5 N6 N7 1.0(2)
C4 C5 N6 N7 -178.6(2)
C5 N6 N7 C8 -.4(2)
N6 N7 C8 N9 -.4(2)
N6 N7 C8 C2' -179.6(2)
C6' N1' C2' C3' -.5(3)
C6' N1' C2' C8 -179.4(2)
N7 C8 C2' N1' 136.0(2)
N9 C8 C2' N1' -43.1(3)
N7 C8 C2' C3' -43.0(3)
N9 C8 C2' C3' 137.9(2)
N1' C2' C3' C4' .9(4)
C8 C2' C3' C4' 179.8(2)
C2' C3' C4' C5' -.8(4)
C3' C4' C5' C6' .4(4)
C2' N1' C6' C5' .1(4)
C4' C5' C6' N1' .0(4)
N6 C5 N9 C8 -1.1(2)
C4 C5 N9 C8 178.4(2)
N6 C5 N9 C10 -170.4(2)
C4 C5 N9 C10 9.2(3)
N7 C8 N9 C5 1.0(2)
C2' C8 N9 C5 -179.9(2)
N7 C8 N9 C10 169.7(2)
C2' C8 N9 C10 -11.1(3)
C5 N9 C10 C11 131.4(2)
C8 N9 C10 C11 -35.4(3)
C5 N9 C10 C15 -46.3(2)
C8 N9 C10 C15 146.9(2)
C15 C10 C11 C12 -2.1(3)
N9 C10 C11 C12 -179.8(2)
C10 C11 C12 C13 1.7(3)
C11 C12 C13 C14 .0(3)
C12 C13 C14 C15 -1.2(3)
C11 C10 C15 C14 .8(3)
N9 C10 C15 C14 178.5(2)
C11 C10 C15 C16 -177.0(2)
N9 C10 C15 C16 .7(2)
C13 C14 C15 C10 .8(3)
C13 C14 C15 C16 178.7(2)
C10 C15 C16 N17 66.1(2)
C14 C15 C16 N17 -111.7(2)
C2 C1 N17 C4 .0(2)
C2 C1 N17 C16 -177.3(2)
C3 C4 N17 C1 .2(2)
C5 C4 N17 C1 -178.0(2)
C3 C4 N17 C16 177.7(2)
C5 C4 N17 C16 -.6(2)
C15 C16 N17 C1 112.5(2)
C15 C16 N17 C4 -64.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 14907914
