#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/79/2217989.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_2217989
loop_
_publ_author_name
'Nawazish Ali, Syed'
'Begum, Sabira'
'Winnik, Mitchell A.'
'Lough, Alan J.'
_publ_section_title
;
 2,5-Dimethylhexane-2,5-diyl bis(4-nitrophenyl) dicarbonate
;
_journal_coeditor_code           PV2070
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o694
_journal_paper_doi               10.1107/S1600536808006120
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C22 H24 N2 O10'
_chemical_formula_moiety         'C22 H24 N2 O10'
_chemical_formula_sum            'C22 H24 N2 O10'
_chemical_formula_weight         476.43
_chemical_name_systematic
;
2,5-Dimethylhexane-2,5-diyl bis(4-nitrophenyl) dicarbonate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                92.717(3)
_cell_angle_beta                 98.886(2)
_cell_angle_gamma                92.952(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1829(4)
_cell_length_b                   11.7024(5)
_cell_length_c                   11.8928(6)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     1121.92(9)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0469
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9940
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SORTAV; Blessing, 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5069
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0502
_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)+(0.0508P)²+0.4455P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1320
_reflns_number_gt                3571
_reflns_number_total             5069
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2070.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2217989
_cod_database_fobs_code          2217989
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O1A 0.45560(16) 0.14403(11) 0.12248(12) 0.0314(3) Uani d . 1
O O2A 0.19552(18) 0.20327(12) 0.11199(15) 0.0434(4) Uani d . 1
O O3A 0.40180(16) 0.30199(10) 0.04414(12) 0.0287(3) Uani d . 1
O O4A 0.3070(2) -0.32743(12) 0.32493(14) 0.0421(4) Uani d . 1
O O5A 0.33546(19) -0.21668(14) 0.47827(13) 0.0415(4) Uani d . 1
N N1A 0.3299(2) -0.23269(14) 0.37471(15) 0.0307(4) Uani d . 1
C C1A 0.4142(2) 0.05054(15) 0.18498(16) 0.0250(4) Uani d . 1
C C2A 0.3979(3) 0.06818(16) 0.29791(18) 0.0310(5) Uani d . 1
H H2AA 0.4071 0.1437 0.3323 0.037 Uiso calc R 1
C C3A 0.3682(2) -0.02484(17) 0.36098(17) 0.0299(4) Uani d . 1
H H3AA 0.3569 -0.0146 0.4391 0.036 Uiso calc R 1
C C4A 0.3553(2) -0.13300(15) 0.30750(16) 0.0238(4) Uani d . 1
C C5A 0.3715(2) -0.15112(16) 0.19471(16) 0.0273(4) Uani d . 1
H H5AA 0.3621 -0.2265 0.1602 0.033 Uiso calc R 1
C C6A 0.4016(2) -0.05742(16) 0.13248(17) 0.0277(4) Uani d . 1
H H6AA 0.4135 -0.0676 0.0545 0.033 Uiso calc R 1
C C7A 0.3338(2) 0.21770(15) 0.09375(17) 0.0279(4) Uani d . 1
C C8A 0.3008(2) 0.39869(15) 0.00122(17) 0.0267(4) Uani d . 1
C C9A 0.2301(3) 0.45775(16) 0.09795(18) 0.0333(5) Uani d . 1
H H9AA 0.1359 0.4106 0.1157 0.050 Uiso calc R 1
H H9AB 0.1930 0.5327 0.0751 0.050 Uiso calc R 1
H H9AC 0.3158 0.4681 0.1656 0.050 Uiso calc R 1
C C10A 0.1670(3) 0.35357(17) -0.09497(19) 0.0351(5) Uani d . 1
H H10A 0.0844 0.3054 -0.0646 0.053 Uiso calc R 1
H H10B 0.2164 0.3080 -0.1508 0.053 Uiso calc R 1
H H10C 0.1133 0.4180 -0.1319 0.053 Uiso calc R 1
C C11A 0.4289(2) 0.47525(15) -0.04470(16) 0.0267(4) Uani d . 1
H H11A 0.4752 0.4303 -0.1037 0.032 Uiso calc R 1
H H11B 0.3722 0.5393 -0.0822 0.032 Uiso calc R 1
O O1B 0.96232(16) -0.15529(11) 0.35566(12) 0.0303(3) Uani d . 1
O O2B 0.70189(17) -0.19261(12) 0.39066(14) 0.0420(4) Uani d . 1
O O3B 0.91508(15) -0.30493(10) 0.44521(11) 0.0261(3) Uani d . 1
O O4B 0.8268(2) 0.33919(12) 0.20273(13) 0.0450(4) Uani d . 1
O O5B 0.82071(18) 0.25161(11) 0.03819(12) 0.0338(3) Uani d . 1
N N1B 0.8330(2) 0.25233(13) 0.14248(14) 0.0272(4) Uani d . 1
C C1B 0.9163(2) -0.05454(15) 0.30242(17) 0.0252(4) Uani d . 1
C C2B 0.9283(2) -0.05045(15) 0.18834(17) 0.0274(4) Uani d . 1
H H2BA 0.9575 -0.1159 0.1471 0.033 Uiso calc R 1
C C3B 0.8973(2) 0.05059(15) 0.13453(16) 0.0263(4) Uani d . 1
H H3BA 0.9031 0.0553 0.0557 0.032 Uiso calc R 1
C C4B 0.8580(2) 0.14393(14) 0.19799(16) 0.0235(4) Uani d . 1
C C5B 0.8458(2) 0.14058(16) 0.31213(16) 0.0265(4) Uani d . 1
H H5BA 0.8184 0.2064 0.3535 0.032 Uiso calc R 1
C C6B 0.8747(2) 0.03886(16) 0.36517(17) 0.0285(4) Uani d . 1
H H6BA 0.8659 0.0335 0.4435 0.034 Uiso calc R 1
C C7B 0.8420(2) -0.21728(15) 0.39835(17) 0.0265(4) Uani d . 1
C C8B 0.8149(2) -0.39774(15) 0.49142(16) 0.0238(4) Uani d . 1
C C9B 0.6938(2) -0.45765(16) 0.39468(18) 0.0313(5) Uani d . 1
H H9BA 0.6058 -0.4066 0.3693 0.047 Uiso calc R 1
H H9BB 0.6450 -0.5278 0.4211 0.047 Uiso calc R 1
H H9BC 0.7521 -0.4773 0.3310 0.047 Uiso calc R 1
C C10B 0.7291(3) -0.34772(17) 0.58539(18) 0.0326(5) Uani d . 1
H H10D 0.6399 -0.3011 0.5521 0.049 Uiso calc R 1
H H10E 0.8095 -0.2998 0.6396 0.049 Uiso calc R 1
H H10F 0.6825 -0.4101 0.6251 0.049 Uiso calc R 1
C C11B 0.9494(2) -0.47459(15) 0.54251(16) 0.0253(4) Uani d . 1
H H11C 1.0257 -0.4294 0.6031 0.030 Uiso calc R 1
H H11D 0.8965 -0.5381 0.5787 0.030 Uiso calc R 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
C7A O1A C1A . 116.31(14)
C7A O3A C8A . 120.17(14)
O4A N1A O5A . 123.51(16)
O4A N1A C4A . 118.20(16)
O5A N1A C4A . 118.28(17)
C6A C1A C2A . 121.84(16)
C6A C1A O1A . 118.27(17)
C2A C1A O1A . 119.75(17)
C1A C2A C3A . 119.51(18)
C1A C2A H2AA . 120.2
C3A C2A H2AA . 120.2
C4A C3A C2A . 118.28(18)
C4A C3A H3AA . 120.9
C2A C3A H3AA . 120.9
C5A C4A C3A . 122.46(16)
C5A C4A N1A . 118.76(16)
C3A C4A N1A . 118.74(17)
C4A C5A C6A . 118.76(17)
C4A C5A H5AA . 120.6
C6A C5A H5AA . 120.6
C1A C6A C5A . 119.15(18)
C1A C6A H6AA . 120.4
C5A C6A H6AA . 120.4
O2A C7A O3A . 129.64(17)
O2A C7A O1A . 124.14(16)
O3A C7A O1A . 106.22(15)
O3A C8A C10A . 109.33(15)
O3A C8A C9A . 110.37(15)
C10A C8A C9A . 112.18(17)
O3A C8A C11A . 101.78(14)
C10A C8A C11A . 110.03(16)
C9A C8A C11A . 112.64(16)
C8A C9A H9AA . 109.5
C8A C9A H9AB . 109.5
H9AA C9A H9AB . 109.5
C8A C9A H9AC . 109.5
H9AA C9A H9AC . 109.5
H9AB C9A H9AC . 109.5
C8A C10A H10A . 109.5
C8A C10A H10B . 109.5
H10A C10A H10B . 109.5
C8A C10A H10C . 109.5
H10A C10A H10C . 109.5
H10B C10A H10C . 109.5
C11A C11A C8A 2_665 114.72(19)
C11A C11A H11A 2_665 108.6
C8A C11A H11A . 108.6
C11A C11A H11B 2_665 108.6
C8A C11A H11B . 108.6
H11A C11A H11B . 107.6
C7B O1B C1B . 117.15(14)
C7B O3B C8B . 120.21(14)
O4B N1B O5B . 123.32(15)
O4B N1B C4B . 118.17(16)
O5B N1B C4B . 118.51(15)
C2B C1B C6B . 122.14(16)
C2B C1B O1B . 117.05(16)
C6B C1B O1B . 120.58(17)
C1B C2B C3B . 119.05(17)
C1B C2B H2BA . 120.5
C3B C2B H2BA . 120.5
C4B C3B C2B . 118.51(17)
C4B C3B H3BA . 120.7
C2B C3B H3BA . 120.7
C3B C4B C5B . 122.79(16)
C3B C4B N1B . 118.54(16)
C5B C4B N1B . 118.65(16)
C4B C5B C6B . 118.48(17)
C4B C5B H5BA . 120.8
C6B C5B H5BA . 120.8
C1B C6B C5B . 119.02(18)
C1B C6B H6BA . 120.5
C5B C6B H6BA . 120.5
O2B C7B O3B . 130.08(17)
O2B C7B O1B . 124.12(16)
O3B C7B O1B . 105.79(15)
O3B C8B C9B . 109.34(14)
O3B C8B C10B . 110.06(14)
C9B C8B C10B . 112.45(16)
O3B C8B C11B . 101.83(14)
C9B C8B C11B . 113.03(15)
C10B C8B C11B . 109.62(15)
C8B C9B H9BA . 109.5
C8B C9B H9BB . 109.5
H9BA C9B H9BB . 109.5
C8B C9B H9BC . 109.5
H9BA C9B H9BC . 109.5
H9BB C9B H9BC . 109.5
C8B C10B H10D . 109.5
C8B C10B H10E . 109.5
H10D C10B H10E . 109.5
C8B C10B H10F . 109.5
H10D C10B H10F . 109.5
H10E C10B H10F . 109.5
C11B C11B C8B 2_746 114.71(19)
C11B C11B H11C 2_746 108.6
C8B C11B H11C . 108.6
C11B C11B H11D 2_746 108.6
C8B C11B H11D . 108.6
H11C C11B H11D . 107.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1A C7A . 1.366(2)
O1A C1A . 1.407(2)
O2A C7A . 1.190(2)
O3A C7A . 1.316(2)
O3A C8A . 1.498(2)
O4A N1A . 1.223(2)
O5A N1A . 1.230(2)
N1A C4A . 1.469(2)
C1A C6A . 1.374(3)
C1A C2A . 1.377(3)
C2A C3A . 1.383(3)
C2A H2AA . 0.9500
C3A C4A . 1.381(3)
C3A H3AA . 0.9500
C4A C5A . 1.376(3)
C5A C6A . 1.384(2)
C5A H5AA . 0.9500
C6A H6AA . 0.9500
C8A C10A . 1.511(3)
C8A C9A . 1.519(3)
C8A C11A . 1.525(3)
C9A H9AA . 0.9800
C9A H9AB . 0.9800
C9A H9AC . 0.9800
C10A H10A . 0.9800
C10A H10B . 0.9800
C10A H10C . 0.9800
C11A C11A 2_665 1.520(4)
C11A H11A . 0.9900
C11A H11B . 0.9900
O1B C7B . 1.367(2)
O1B C1B . 1.406(2)
O2B C7B . 1.187(2)
O3B C7B . 1.317(2)
O3B C8B . 1.502(2)
O4B N1B . 1.223(2)
O5B N1B . 1.228(2)
N1B C4B . 1.467(2)
C1B C2B . 1.378(3)
C1B C6B . 1.381(3)
C2B C3B . 1.387(2)
C2B H2BA . 0.9500
C3B C4B . 1.378(3)
C3B H3BA . 0.9500
C4B C5B . 1.379(3)
C5B C6B . 1.387(2)
C5B H5BA . 0.9500
C6B H6BA . 0.9500
C8B C9B . 1.516(3)
C8B C10B . 1.519(3)
C8B C11B . 1.528(2)
C9B H9BA . 0.9800
C9B H9BB . 0.9800
C9B H9BC . 0.9800
C10B H10D . 0.9800
C10B H10E . 0.9800
C10B H10F . 0.9800
C11B C11B 2_746 1.521(4)
C11B H11C . 0.9900
C11B H11D . 0.9900
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
C5A H5AA O5B 2_655 0.95 2.59 3.112(2) 115
C5B H5BA O5A 2_656 0.95 2.52 3.205(2) 129
C11A H11B O3A 2_665 0.99 2.53 2.888(2) 101
C11A H11B O4B 2_665 0.99 2.54 3.502(2) 165
C11B H11C O4B 2_756 0.99 2.58 3.546(2) 164
C11B H11D O3B 2_746 0.99 2.49 2.862(2) 102
