#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:34:44 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179668 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/21/4512178.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_4512178
loop_
_publ_author_name
'Manner, Virginia W.'
'Tappan, Bryce C.'
'Scott, Brian L.'
'Preston, Daniel N.'
'Brown, Geoffrey W.'
_publ_section_title
;
 Crystal Structure, Packing Analysis, and Structural-Sensitivity
 Correlations of Erythritol Tetranitrate
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              6154
_journal_paper_doi               10.1021/cg501362b
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C4 H6 N4 O12'
_chemical_formula_weight         302.13
_chemical_name_systematic
; 
 ? 
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.161(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.893(6)
_cell_length_b                   5.1595(19)
_cell_length_c                   14.731(5)
_cell_measurement_temperature    140(1)
_cell_volume                     1084.2(7)
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       '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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10239
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.11
_diffrn_reflns_theta_min         2.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  0.9737
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0357
_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)+(0.0574P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1026
_reflns_number_gt                2141
_reflns_number_total             2521
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501362b_si_001.cif
_cod_data_source_block           apx1740a
_cod_depositor_comments          'Adding full bibliography for 4512178.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4512178
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_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 0.32278(7) 0.7322(2) 0.86523(8) 0.0202(2) Uani 1 1 d .
N2 N 0.41133(7) 1.1061(2) 1.19931(7) 0.0225(2) Uani 1 1 d .
N4 N 0.08919(7) 0.4250(2) 0.28509(7) 0.0233(3) Uani 1 1 d .
N3 N 0.17888(7) 0.75890(19) 0.03469(7) 0.0195(2) Uani 1 1 d .
O1 O 0.41186(6) 0.75670(15) 0.95047(6) 0.0184(2) Uani 1 1 d .
O2 O 0.28571(7) 0.92690(18) 0.82046(7) 0.0298(2) Uani 1 1 d .
O3 O 0.29706(7) 0.51288(17) 0.85040(7) 0.0259(2) Uani 1 1 d .
O4 O 0.43712(6) 0.99978(16) 1.12803(6) 0.0208(2) Uani 1 1 d .
O5 O 0.37026(6) 1.30842(19) 1.18044(6) 0.0264(2) Uani 1 1 d .
O6 O 0.43557(7) 0.9719(2) 1.27381(7) 0.0344(3) Uani 1 1 d .
O7 O 0.08972(6) 0.74007(15) 0.03522(6) 0.0183(2) Uani 1 1 d .
O8 O 0.21040(6) 0.57041(18) 0.01412(7) 0.0272(2) Uani 1 1 d .
O9 O 0.21026(7) 0.97425(17) 0.05554(7) 0.0272(2) Uani 1 1 d .
O10 O 0.06316(6) 0.51841(16) 0.18730(6) 0.0199(2) Uani 1 1 d .
O11 O 0.12606(7) 0.21768(19) 0.30735(7) 0.0296(2) Uani 1 1 d .
O12 O 0.06963(7) 0.5751(2) 0.33555(7) 0.0349(3) Uani 1 1 d .
C1 C 0.44648(8) 1.0199(2) 0.97315(9) 0.0160(3) Uani 1 1 d .
H1 H 0.4293 1.1163 0.9101 0.019 Uiso 1 1 calc R
C2 C 0.40689(8) 1.1548(2) 1.03716(8) 0.0175(3) Uani 1 1 d .
H2A H 0.4311 1.3300 1.0534 0.021 Uiso 1 1 calc R
H2B H 0.3390 1.1620 1.0019 0.021 Uiso 1 1 calc R
C3 C 0.05339(8) 0.4790(2) 0.02471(9) 0.0159(3) Uani 1 1 d .
H3 H 0.0712 0.3792 -0.0207 0.019 Uiso 1 1 calc R
C4 C 0.09166(8) 0.3497(2) 0.12736(8) 0.0173(2) Uani 1 1 d .
H4A H 0.0653 0.1777 0.1223 0.021 Uiso 1 1 calc R
H4B H 0.1594 0.3358 0.1567 0.021 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_3
O3 N1 O2 130.35(11) .
O3 N1 O1 111.93(9) .
O2 N1 O1 117.72(10) .
O5 N2 O6 129.30(11) .
O5 N2 O4 118.59(9) .
O6 N2 O4 112.10(10) .
O11 N4 O12 129.43(11) .
O11 N4 O10 118.59(10) .
O12 N4 O10 111.98(11) .
O8 N3 O9 130.23(11) .
O8 N3 O7 118.44(9) .
O9 N3 O7 111.33(9) .
N1 O1 C1 114.54(8) .
N2 O4 C2 112.98(9) .
N3 O7 C3 114.47(8) .
N4 O10 C4 113.04(9) .
O1 C1 C2 110.79(9) .
O1 C1 C1 102.37(11) 3_677
C2 C1 C1 114.16(12) 3_677
O4 C2 C1 105.21(9) .
O7 C3 C4 109.75(9) .
O7 C3 C3 102.98(11) 3_565
C4 C3 C3 114.10(12) 3_565
O10 C4 C3 104.38(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 O3 1.1902(13) .
N1 O2 1.2035(14) .
N1 O1 1.4246(13) .
N2 O5 1.1971(15) .
N2 O6 1.2080(14) .
N2 O4 1.3968(13) .
N4 O11 1.1938(15) .
N4 O12 1.2052(14) .
N4 O10 1.3976(13) .
N3 O8 1.1927(14) .
N3 O9 1.2010(13) .
N3 O7 1.4237(14) .
O1 C1 1.4481(14) .
O4 C2 1.4476(14) .
O7 C3 1.4466(14) .
O10 C4 1.4475(14) .
C1 C2 1.5142(16) .
C1 C1 1.541(2) 3_677
C3 C4 1.5135(16) .
C3 C3 1.539(2) 3_565
