#------------------------------------------------------------------------------
#$Date: 2016-11-08 21:56:22 +0200 (Tue, 08 Nov 2016) $
#$Revision: 188197 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/09/7040955.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_7040955
loop_
_publ_author_name
'Feng, Yong-An'
'Qiu, Hao'
'Yang, Sa-Sha'
'Du, Jiang'
'Zhang, Tong-Lai'
_publ_section_title
;
 Carbonyl-bridged energetic materials: biomimetic synthesis, organic
 catalytic synthesis, and energetic performances.
;
_journal_issue                   43
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17117
_journal_page_last               17122
_journal_paper_doi               10.1039/c6dt03271k
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C5 H14 N14'
_chemical_formula_weight         270.30
_chemical_name_systematic        G2btm
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-07-30 deposited with the CCDC.
2016-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.452(4)
_cell_length_b                   4.6313(13)
_cell_length_c                   17.861(5)
_cell_measurement_reflns_used    4736
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      31.492
_cell_measurement_theta_min      2.280
_cell_volume                     1195.5(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            11071
_diffrn_reflns_theta_full        31.49
_diffrn_reflns_theta_max         31.49
_diffrn_reflns_theta_min         2.82
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Chip
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(17)
_refine_ls_extinction_coef       0.0085(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3594
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0396
_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)+(0.0440P)²+0.1190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                3266
_reflns_number_total             3594
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt03271k2.cif
_cod_data_source_block           bn4390
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7040954--7040958.cif.
;
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               7040955
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
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
N1 N 0.50236(9) 0.9669(3) 0.17167(8) 0.0235(3) Uani 1 1 d .
N2 N 0.46623(9) 0.8386(3) 0.11098(7) 0.0257(3) Uani 1 1 d .
N3 N 0.50704(10) 0.9352(3) 0.05038(8) 0.0269(3) Uani 1 1 d .
N4 N 0.57210(10) 1.1315(3) 0.07026(7) 0.0259(3) Uani 1 1 d .
N5 N 0.75224(10) 0.9627(3) 0.21970(8) 0.0234(3) Uani 1 1 d .
N6 N 0.78232(10) 0.8258(3) 0.28169(8) 0.0267(3) Uani 1 1 d .
N7 N 0.73525(11) 0.9171(3) 0.33968(8) 0.0302(3) Uani 1 1 d .
N8 N 0.67264(11) 1.1179(3) 0.31763(7) 0.0291(3) Uani 1 1 d .
N9 N 0.67228(10) 0.6163(3) 0.59715(7) 0.0245(3) Uani 1 1 d .
N10 N 0.74285(10) 0.8723(3) 0.50223(8) 0.0277(3) Uani 1 1 d .
N11 N 0.63852(11) 0.5136(3) 0.47377(8) 0.0268(3) Uani 1 1 d .
N12 N 0.88612(10) 0.4082(3) 0.42202(8) 0.0258(3) Uani 1 1 d .
N13 N 0.92676(10) 0.3662(3) 0.29789(7) 0.0253(3) Uani 1 1 d .
N14 N 0.98444(10) 0.0457(3) 0.38504(7) 0.0248(3) Uani 1 1 d .
C1 C 0.56689(10) 1.1451(3) 0.14509(8) 0.0202(3) Uani 1 1 d .
C2 C 0.62871(12) 1.3267(3) 0.19345(10) 0.0236(3) Uani 1 1 d .
H2A H 0.6700 1.4444 0.1614 0.028 Uiso 1 1 calc R
H2B H 0.5906 1.4596 0.2240 0.028 Uiso 1 1 calc R
C3 C 0.68568(10) 1.1391(3) 0.24383(8) 0.0198(3) Uani 1 1 d .
C4 C 0.68470(10) 0.6690(3) 0.52506(7) 0.0203(3) Uani 1 1 d .
C5 C 0.93275(10) 0.2743(3) 0.36796(7) 0.0196(3) Uani 1 1 d .
H9A H 0.6308(12) 0.482(4) 0.6111(12) 0.023(5) Uiso 1 1 d .
H9B H 0.6968(14) 0.752(5) 0.6320(12) 0.044(6) Uiso 1 1 d .
H10A H 0.7809(13) 0.969(4) 0.5378(14) 0.034(6) Uiso 1 1 d .
H10B H 0.7493(14) 0.911(4) 0.4505(14) 0.032(5) Uiso 1 1 d .
H11A H 0.6016(16) 0.374(5) 0.4925(13) 0.040(6) Uiso 1 1 d .
H11B H 0.6554(14) 0.512(4) 0.4291(13) 0.033(5) Uiso 1 1 d .
H12A H 0.8935(14) 0.362(4) 0.4697(13) 0.037(5) Uiso 1 1 d .
H12B H 0.8466(16) 0.575(5) 0.4102(14) 0.051(7) Uiso 1 1 d .
H13A H 0.8896(16) 0.502(5) 0.2905(15) 0.046(7) Uiso 1 1 d .
H13B H 0.9455(18) 0.259(7) 0.2617(17) 0.069(8) Uiso 1 1 d .
H14A H 0.9874(15) 0.007(5) 0.4332(14) 0.038(6) Uiso 1 1 d .
H14B H 1.0230(18) -0.027(5) 0.3564(18) 0.055(8) Uiso 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
C1 N1 N2 104.99(13)
N3 N2 N1 109.91(13)
N2 N3 N4 108.95(13)
C1 N4 N3 104.71(13)
C3 N5 N6 104.79(13)
N7 N6 N5 109.27(13)
N6 N7 N8 109.78(13)
C3 N8 N7 104.07(14)
C4 N9 H9A 119.2(13)
C4 N9 H9B 117.6(13)
H9A N9 H9B 121.6(18)
C4 N10 H10A 119.6(13)
C4 N10 H10B 119.8(13)
H10A N10 H10B 120.4(18)
C4 N11 H11A 115.2(15)
C4 N11 H11B 120.7(14)
H11A N11 H11B 121(2)
C5 N12 H12A 121.7(14)
C5 N12 H12B 120.3(15)
H12A N12 H12B 118(2)
C5 N13 H13A 115.6(19)
C5 N13 H13B 120(2)
H13A N13 H13B 121(3)
C5 N14 H14A 114.5(15)
C5 N14 H14B 124(2)
H14A N14 H14B 119(3)
N1 C1 N4 111.44(14)
N1 C1 C2 123.96(14)
N4 C1 C2 124.54(14)
C3 C2 C1 110.37(11)
C3 C2 H2A 109.6
C1 C2 H2A 109.6
C3 C2 H2B 109.6
C1 C2 H2B 109.6
H2A C2 H2B 108.1
N5 C3 N8 112.08(14)
N5 C3 C2 123.89(14)
N8 C3 C2 123.94(15)
N9 C4 N10 121.06(14)
N9 C4 N11 119.87(14)
N10 C4 N11 119.07(14)
N13 C5 N12 120.18(13)
N13 C5 N14 120.58(13)
N12 C5 N14 119.23(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3326(19)
N1 N2 1.3420(19)
N2 N3 1.3113(19)
N3 N4 1.3550(19)
N4 C1 1.3400(19)
N5 C3 1.333(2)
N5 N6 1.3482(19)
N6 N7 1.310(2)
N7 N8 1.356(2)
N8 C3 1.3351(18)
N9 C4 1.3227(18)
N9 H9A 0.898(19)
N9 H9B 0.95(2)
N10 C4 1.3264(19)
N10 H10A 0.95(2)
N10 H10B 0.95(2)
N11 C4 1.3425(19)
N11 H11A 0.90(2)
N11 H11B 0.83(2)
N12 C5 1.3308(19)
N12 H12A 0.88(2)
N12 H12B 0.98(2)
N13 C5 1.3247(18)
N13 H13A 0.84(2)
N13 H13B 0.86(3)
N14 C5 1.3314(19)
N14 H14A 0.88(2)
N14 H14B 0.83(3)
C1 C2 1.501(2)
C2 C3 1.498(2)
C2 H2A 0.9900
C2 H2B 0.9900
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
C1 N1 N2 N3 -0.08(17)
N1 N2 N3 N4 0.21(17)
N2 N3 N4 C1 -0.25(16)
C3 N5 N6 N7 0.19(16)
N5 N6 N7 N8 -0.09(18)
N6 N7 N8 C3 -0.06(18)
N2 N1 C1 N4 -0.09(17)
N2 N1 C1 C2 -177.36(13)
N3 N4 C1 N1 0.21(17)
N3 N4 C1 C2 177.46(13)
N1 C1 C2 C3 60.5(2)
N4 C1 C2 C3 -116.43(16)
N6 N5 C3 N8 -0.24(17)
N6 N5 C3 C2 -177.05(13)
N7 N8 C3 N5 0.19(18)
N7 N8 C3 C2 177.00(13)
C1 C2 C3 N5 67.8(2)
C1 C2 C3 N8 -108.64(17)
