#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/59/2225907.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_2225907
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Yathirajan, H. S.'
'Narayana, B.'
'Prakash Kamath, K.'
_publ_section_title
;
 5,7-Dimethyl-2,3-dihydro-1H-1,4-diazepin-4-ium picrate
;
_journal_coeditor_code           IS2536
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1187
_journal_page_last               o1188
_journal_paper_doi               10.1107/S160053681001487X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H13 N2 +, C6 H2 N3 O7-'
_chemical_formula_moiety         'C7 H13 N2 +, C6 H2 N3 O7-'
_chemical_formula_sum            'C13 H15 N5 O7'
_chemical_formula_weight         353.30
_chemical_name_systematic
;
5,7-Dimethyl-2,3-dihydro-1H-1,4-diazepin-4-ium picrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 110.611(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2341(3)
_cell_length_b                   27.6458(6)
_cell_length_c                   8.2831(3)
_cell_measurement_reflns_used    9544
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      34.6885
_cell_measurement_theta_min      4.6914
_cell_volume                     1550.52(10)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24773
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         34.77
_diffrn_reflns_theta_min         4.70
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         6353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0740P)²+0.3582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1501
_reflns_number_gt                4493
_reflns_number_total             6353
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2536.cif
_cod_data_source_block           I
_cod_original_cell_volume        1550.52(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2225907
_cod_database_fobs_code          2225907
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
O O1A 0.30761(14) 0.42368(3) 0.49438(11) 0.02584(19) Uani d . 1 . .
O O21A 0.1166(2) 0.37603(5) 0.19050(14) 0.0569(4) Uani d . 1 . .
O O22A 0.2759(3) 0.30970(5) 0.20409(16) 0.0696(5) Uani d . 1 . .
O O41A 0.2539(2) 0.20668(4) 0.67603(15) 0.0493(3) Uani d . 1 . .
O O42A 0.2899(2) 0.23953(4) 0.92133(14) 0.0444(3) Uani d . 1 . .
O O61A 0.4592(2) 0.41131(4) 0.99837(13) 0.0466(3) Uani d . 1 . .
O O62A 0.26070(17) 0.45405(3) 0.79164(13) 0.0374(2) Uani d . 1 . .
N N2A 0.2123(2) 0.34203(4) 0.27069(14) 0.0367(3) Uani d . 1 . .
N N4A 0.27398(18) 0.24249(4) 0.76838(15) 0.0295(2) Uani d . 1 . .
N N6A 0.34729(18) 0.41624(4) 0.84935(13) 0.0257(2) Uani d . 1 . .
C C1A 0.28914(16) 0.38355(4) 0.55484(14) 0.0188(2) Uani d . 1 . .
C C2A 0.25139(19) 0.33908(4) 0.45574(14) 0.0230(2) Uani d . 1 . .
C C3A 0.2521(2) 0.29387(4) 0.52339(15) 0.0247(2) Uani d . 1 . .
H H3AA 0.2331 0.2660 0.4524 0.030 Uiso calc R 1 . .
C C4A 0.28112(19) 0.28952(4) 0.69802(15) 0.0224(2) Uani d . 1 . .
C C5A 0.31328(18) 0.32993(4) 0.80487(15) 0.0213(2) Uani d . 1 . .
H H5AA 0.3340 0.3265 0.9241 0.026 Uiso calc R 1 . .
C C6A 0.31432(17) 0.37484(4) 0.73403(14) 0.0194(2) Uani d . 1 . .
C C7B 0.2662(3) 0.50023(5) 0.18073(19) 0.0357(3) Uani d . 1 . .
H H7BA 0.2199 0.4691 0.2088 0.054 Uiso calc R 1 . .
H H7BB 0.4074 0.4981 0.1993 0.054 Uiso calc R 1 . .
H H7BC 0.1929 0.5082 0.0597 0.054 Uiso calc R 1 . .
N N1B 0.23246(16) 0.52460(3) 0.44657(14) 0.0252(2) Uani d . 1 . .
H H1BC 0.2648 0.4943 0.4762 0.030 Uiso calc R 1 . .
N N2B 0.24482(17) 0.63760(3) 0.48145(13) 0.0250(2) Uani d . 1 . .
H H2BC 0.2328 0.6674 0.5141 0.030 Uiso calc R 1 . .
C C1B 0.1824(2) 0.55501(4) 0.56818(17) 0.0277(3) Uani d . 1 . .
H H1BA 0.2014 0.5362 0.6746 0.033 Uiso calc R 1 . .
H H1BB 0.0409 0.5638 0.5178 0.033 Uiso calc R 1 . .
C C2B 0.3044(2) 0.60105(4) 0.61571(16) 0.0267(2) Uani d . 1 . .
H H2BA 0.2927 0.6146 0.7223 0.032 Uiso calc R 1 . .
H H2BB 0.4450 0.5929 0.6406 0.032 Uiso calc R 1 . .
C C3B 0.20682(17) 0.63060(4) 0.31478(15) 0.0212(2) Uani d . 1 . .
C C4B 0.1720(2) 0.67590(4) 0.20732(17) 0.0283(3) Uani d . 1 . .
H H4BA 0.1655 0.7038 0.2782 0.042 Uiso calc R 1 . .
H H4BB 0.0472 0.6730 0.1098 0.042 Uiso calc R 1 . .
H H4BC 0.2806 0.6804 0.1640 0.042 Uiso calc R 1 . .
C C5B 0.20560(19) 0.58659(4) 0.23242(15) 0.0236(2) Uani d . 1 . .
H H5BA 0.1819 0.5893 0.1125 0.028 Uiso calc R 1 . .
C C6B 0.23301(18) 0.53901(4) 0.29478(16) 0.0236(2) Uani d . 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'
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
O21A N2A O22A . . 123.42(13) ?
O21A N2A C2A . . 118.62(12) ?
O22A N2A C2A . . 117.95(12) ?
O41A N4A O42A . . 122.28(11) ?
O41A N4A C4A . . 119.43(11) ?
O42A N4A C4A . . 118.29(10) ?
O61A N6A O62A . . 123.71(11) ?
O61A N6A C6A . . 118.17(10) ?
O62A N6A C6A . . 118.12(10) ?
O1A C1A C2A . . 123.64(10) ?
O1A C1A C6A . . 124.58(10) ?
C2A C1A C6A . . 111.68(9) ?
C3A C2A C1A . . 124.72(10) ?
C3A C2A N2A . . 116.88(10) ?
C1A C2A N2A . . 118.39(10) ?
C2A C3A C4A . . 118.80(10) ?
C2A C3A H3AA . . 120.6 ?
C4A C3A H3AA . . 120.6 ?
C3A C4A C5A . . 121.43(10) ?
C3A C4A N4A . . 119.15(10) ?
C5A C4A N4A . . 119.41(10) ?
C6A C5A C4A . . 118.55(10) ?
C6A C5A H5AA . . 120.7 ?
C4A C5A H5AA . . 120.7 ?
C5A C6A C1A . . 124.70(10) ?
C5A C6A N6A . . 117.03(10) ?
C1A C6A N6A . . 118.26(9) ?
C6B C7B H7BA . . 109.5 ?
C6B C7B H7BB . . 109.5 ?
H7BA C7B H7BB . . 109.5 ?
C6B C7B H7BC . . 109.5 ?
H7BA C7B H7BC . . 109.5 ?
H7BB C7B H7BC . . 109.5 ?
C6B N1B C1B . . 124.82(10) ?
C6B N1B H1BC . . 117.6 ?
C1B N1B H1BC . . 117.6 ?
C3B N2B C2B . . 126.45(10) ?
C3B N2B H2BC . . 116.8 ?
C2B N2B H2BC . . 116.8 ?
N1B C1B C2B . . 113.60(10) ?
N1B C1B H1BA . . 108.8 ?
C2B C1B H1BA . . 108.8 ?
N1B C1B H1BB . . 108.8 ?
C2B C1B H1BB . . 108.8 ?
H1BA C1B H1BB . . 107.7 ?
N2B C2B C1B . . 113.33(11) ?
N2B C2B H2BA . . 108.9 ?
C1B C2B H2BA . . 108.9 ?
N2B C2B H2BB . . 108.9 ?
C1B C2B H2BB . . 108.9 ?
H2BA C2B H2BB . . 107.7 ?
N2B C3B C5B . . 126.98(10) ?
N2B C3B C4B . . 115.16(10) ?
C5B C3B C4B . . 117.78(10) ?
C3B C4B H4BA . . 109.5 ?
C3B C4B H4BB . . 109.5 ?
H4BA C4B H4BB . . 109.5 ?
C3B C4B H4BC . . 109.5 ?
H4BA C4B H4BC . . 109.5 ?
H4BB C4B H4BC . . 109.5 ?
C3B C5B C6B . . 131.55(11) ?
C3B C5B H5BA . . 114.2 ?
C6B C5B H5BA . . 114.2 ?
N1B C6B C5B . . 125.93(11) ?
N1B C6B C7B . . 115.97(11) ?
C5B C6B C7B . . 118.10(11) ?
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
O1A C1A . 1.2438(13) ?
O21A N2A . 1.2165(17) ?
O22A N2A . 1.2219(18) ?
O41A N4A . 1.2281(15) ?
O42A N4A . 1.2338(15) ?
O61A N6A . 1.2223(15) ?
O62A N6A . 1.2257(14) ?
N2A C2A . 1.4597(15) ?
N4A C4A . 1.4332(14) ?
N6A C6A . 1.4558(14) ?
C1A C2A . 1.4496(15) ?
C1A C6A . 1.4504(15) ?
C2A C3A . 1.3692(16) ?
C3A C4A . 1.3918(16) ?
C3A H3AA . 0.9500 ?
C4A C5A . 1.3929(15) ?
C5A C6A . 1.3744(15) ?
C5A H5AA . 0.9500 ?
C7B C6B . 1.5031(17) ?
C7B H7BA . 0.9800 ?
C7B H7BB . 0.9800 ?
C7B H7BC . 0.9800 ?
N1B C6B . 1.3202(16) ?
N1B C1B . 1.4524(16) ?
N1B H1BC . 0.8800 ?
N2B C3B . 1.3235(15) ?
N2B C2B . 1.4512(15) ?
N2B H2BC . 0.8800 ?
C1B C2B . 1.5199(18) ?
C1B H1BA . 0.9900 ?
C1B H1BB . 0.9900 ?
C2B H2BA . 0.9900 ?
C2B H2BB . 0.9900 ?
C3B C5B . 1.3935(15) ?
C3B C4B . 1.5055(16) ?
C4B H4BA . 0.9800 ?
C4B H4BB . 0.9800 ?
C4B H4BC . 0.9800 ?
C5B C6B . 1.4014(16) ?
C5B H5BA . 0.9500 ?
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
N1B H1BC O1A . 0.88 1.98 2.8434(13) 168.7
N2B H2BC O42A 2_556 0.88 2.09 2.9657(14) 176.3
C5A H5AA O22A 1_556 0.95 2.54 3.4570(16) 161.9
C7B H7BA O1A . 0.98 2.55 3.2817(17) 131.1
C1B H1BA O62A . 0.99 2.45 3.2861(15) 142.2
C1B H1BB O1A 3_566 0.99 2.51 3.4477(16) 157.6
C2B H2BA O61A 3_667 0.99 2.48 3.0678(16) 117.4
C2B H2BB O1A 3_666 0.99 2.46 3.3135(16) 143.6
C4B H4BA O42A 2_556 0.98 2.59 3.4692(17) 149.3
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
O1A C1A C2A C3A . . . . 172.43(12) ?
C6A C1A C2A C3A . . . . -4.09(18) ?
O1A C1A C2A N2A . . . . -6.66(18) ?
C6A C1A C2A N2A . . . . 176.82(11) ?
O21A N2A C2A C3A . . . . 143.77(15) ?
O22A N2A C2A C3A . . . . -35.4(2) ?
O21A N2A C2A C1A . . . . -37.07(19) ?
O22A N2A C2A C1A . . . . 143.81(15) ?
C1A C2A C3A C4A . . . . 3.4(2) ?
N2A C2A C3A C4A . . . . -177.54(12) ?
C2A C3A C4A C5A . . . . -1.33(19) ?
C2A C3A C4A N4A . . . . 177.46(12) ?
O41A N4A C4A C3A . . . . 4.2(2) ?
O42A N4A C4A C3A . . . . -176.34(13) ?
O41A N4A C4A C5A . . . . -176.96(13) ?
O42A N4A C4A C5A . . . . 2.48(19) ?
C3A C4A C5A C6A . . . . 0.53(19) ?
N4A C4A C5A C6A . . . . -178.27(11) ?
C4A C5A C6A C1A . . . . -1.66(19) ?
C4A C5A C6A N6A . . . . 179.67(11) ?
O1A C1A C6A C5A . . . . -173.26(12) ?
C2A C1A C6A C5A . . . . 3.22(17) ?
O1A C1A C6A N6A . . . . 5.39(18) ?
C2A C1A C6A N6A . . . . -178.13(10) ?
O61A N6A C6A C5A . . . . 34.74(17) ?
O62A N6A C6A C5A . . . . -145.02(12) ?
O61A N6A C6A C1A . . . . -144.01(13) ?
O62A N6A C6A C1A . . . . 36.22(16) ?
C6B N1B C1B C2B . . . . -55.05(17) ?
C3B N2B C2B C1B . . . . -45.65(17) ?
N1B C1B C2B N2B . . . . 75.70(14) ?
C2B N2B C3B C5B . . . . 3.7(2) ?
C2B N2B C3B C4B . . . . -172.89(12) ?
N2B C3B C5B C6B . . . . 3.3(2) ?
C4B C3B C5B C6B . . . . 179.87(13) ?
C1B N1B C6B C5B . . . . 6.9(2) ?
C1B N1B C6B C7B . . . . -173.08(13) ?
C3B C5B C6B N1B . . . . 13.0(2) ?
C3B C5B C6B C7B . . . . -167.02(14) ?
