#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/25/2012530.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_2012530
loop_
_publ_author_name
'Spiniello, Marisa'
'White, Jonathan M.'
_publ_section_title
;
 cis- and
 trans-2-(4-tert-Butylcyclohexyloxy)-1,3,5-trinitrobenzene
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o94
_journal_page_last               o96
_journal_paper_doi               10.1107/S0108270101019400
_journal_volume                  58
_journal_year                    2002
_chemical_formula_moiety         'C16 H21 N3 O7'
_chemical_formula_sum            'C16 H21 N3 O7'
_chemical_formula_weight         367.36
_chemical_melting_point          .382E-305
_chemical_name_common            'cis-4-tert-Butylcyclohexyl Picrate'
_chemical_name_systematic
;
cis-2-(4-tert-butylcyclohexyloxy)-1,3,5-trinitrobenzene
;
_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           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 102.71(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.257(3)
_cell_length_b                   8.954(2)
_cell_length_c                   13.623(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1815.5(6)
_computing_cell_refinement       'Please provide missing details'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'PROCESS_DATA (Gable et al., 1994)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      130.0(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .071
_diffrn_reflns_av_sigmaI/netI    .026
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3341
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.65
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  160
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .1
_refine_diff_density_max         .18
_refine_diff_density_min         -.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          .052
_refine_ls_R_factor_gt           .039
_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)+(0.0547P)²+0.7679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .098
_refine_ls_wR_factor_ref         .107
_reflns_number_gt                2589
_reflns_number_total             3191
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ta1354.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2012530
_cod_database_fobs_code          2012530
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
O1 .35406(7) .10294(13) .38706(8) .0283(3) Uani d . 1 . . O
O2 .42741(9) -.11097(14) .27609(9) .0399(3) Uani d . 1 . . O
O3 .52807(8) -.01119(14) .20653(8) .0373(3) Uani d . 1 . . O
O4 .76546(9) .2442(2) .44099(13) .0684(5) Uani d . 1 . . O
O5 .74124(9) .32672(17) .58197(11) .0499(4) Uani d . 1 . . O
O6 .38102(12) .20593(17) .60027(12) .0608(5) Uani d . 1 . . O
O7 .38321(9) .41883(14) .53021(10) .0418(3) Uani d . 1 . . O
N1 .48488(9) -.01663(16) .27262(10) .0285(3) Uani d . 1 . . N
N2 .71656(10) .26895(19) .49872(13) .0415(4) Uani d . 1 . . N
N3 .40736(9) .29034(15) .54415(9) .0258(3) Uani d . 1 . . N
C1 .29548(11) .1294(2) .28506(11) .0289(4) Uani d . 1 . . C
H1 .3302 .1110 .2319 .035 Uiso calc R 1 . . H
C2 .26267(12) .2886(2) .27957(13) .0334(4) Uani d . 1 . . C
H2A .2325 .3115 .2091 .040 Uiso calc R 1 . . H
H2B .3152 .3559 .2985 .040 Uiso calc R 1 . . H
C3 .19776(12) .3215(2) .34719(13) .0333(4) Uani d . 1 . . C
H3A .1727 .4230 .3323 .040 Uiso calc R 1 . . H
H3B .2311 .3198 .4183 .040 Uiso calc R 1 . . H
C4 .12040(11) .2088(2) .33325(12) .0298(4) Uani d . 1 . . C
H4 .0876 .2153 .2612 .036 Uiso calc R 1 . . H
C5 .16018(11) .0509(2) .34915(12) .0309(4) Uani d . 1 . . C
H5A .1957 .0413 .4190 .037 Uiso calc R 1 . . H
H5B .1108 -.0231 .3396 .037 Uiso calc R 1 . . H
C6 .22027(11) .0175(2) .27564(13) .0324(4) Uani d . 1 . . C
H6A .2460 -.0839 .2889 .039 Uiso calc R 1 . . H
H6B .1836 .0193 .2060 .039 Uiso calc R 1 . . H
C7 .05095(12) .2445(2) .39792(14) .0391(5) Uani d . 1 . . C
C8 -.03041(15) .1422(3) .3667(2) .0672(7) Uani d . 1 . . C
H8A -.0113 .0379 .3776 .101 Uiso calc R 1 . . H
H8B -.0578 .1579 .2954 .101 Uiso calc R 1 . . H
H8C -.0744 .1653 .4072 .101 Uiso calc R 1 . . H
C9 .01795(11) .4061(2) .37967(11) .0538(6) Uani d . 1 . . C
H9A .0689 .4745 .3991 .081 Uiso calc R 1 . . H
H9B -.0264 .4272 .4200 .081 Uiso calc R 1 . . H
H9C -.0097 .4198 .3082 .081 Uiso calc R 1 . . H
C10 .09208(11) .2259(2) .51114(11) .0554(6) Uani d . 1 . . C
H10A .1443 .2919 .5306 .083 Uiso calc R 1 . . H
H10B .1110 .1220 .5250 .083 Uiso calc R 1 . . H
H10C .0472 .2520 .5498 .083 Uiso calc R 1 . . H
C11 .44102(10) .14076(17) .40586(11) .0225(3) Uani d . 1 . . C
C12 .50619(11) .09297(17) .35444(11) .0237(3) Uani d . 1 . . C
C13 .59502(11) .13768(18) .38259(12) .0271(4) Uani d . 1 . . C
H13 .6373 .1072 .3448 .033 Uiso calc R 1 . . H
C14 .62135(11) .22707(19) .46628(12) .0284(4) Uani d . 1 . . C
C15 .56138(11) .27694(18) .52143(12) .0273(4) Uani d . 1 . . C
H15 .5801 .3381 .5792 .033 Uiso calc R 1 . . H
C16 .47322(11) .23401(17) .48883(11) .0231(3) Uani d . 1 . . C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 '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 .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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_publ_flag
C11 O1 C1 120.13(11) y
O2 N1 O3 124.01(14) ?
O2 N1 C12 118.20(13) ?
O3 N1 C12 117.74(14) ?
O4 N2 O5 124.49(16) ?
O4 N2 C14 117.69(16) ?
O5 N2 C14 117.83(15) ?
O6 N3 O7 124.27(14) ?
O6 N3 C16 118.07(13) ?
O7 N3 C16 117.66(13) ?
O1 C1 C6 105.18(13) y
O1 C1 C2 108.65(13) y
C6 C1 C2 112.71(14) ?
O1 C1 H1 110.1 ?
C6 C1 H1 110.1 ?
C2 C1 H1 110.1 ?
C1 C2 C3 113.94(14) y
C1 C2 H2A 108.8 ?
C3 C2 H2A 108.8 ?
C1 C2 H2B 108.8 ?
C3 C2 H2B 108.8 ?
H2A C2 H2B 107.7 ?
C2 C3 C4 112.56(14) y
C2 C3 H3A 109.1 ?
C4 C3 H3A 109.1 ?
C2 C3 H3B 109.1 ?
C4 C3 H3B 109.1 ?
H3A C3 H3B 107.8 ?
C3 C4 C5 108.62(14) y
C3 C4 C7 113.40(15) y
C5 C4 C7 114.04(14) y
C3 C4 H4 106.8 ?
C5 C4 H4 106.8 ?
C7 C4 H4 106.8 ?
C6 C5 C4 111.29(14) y
C6 C5 H5A 109.4 ?
C4 C5 H5A 109.4 ?
C6 C5 H5B 109.4 ?
C4 C5 H5B 109.4 ?
H5A C5 H5B 108.0 ?
C1 C6 C5 111.69(14) y
C1 C6 H6A 109.3 ?
C5 C6 H6A 109.3 ?
C1 C6 H6B 109.3 ?
C5 C6 H6B 109.3 ?
H6A C6 H6B 107.9 ?
C8 C7 C9 107.64(17) ?
C8 C7 C10 109.94(17) ?
C9 C7 C10 108.13(15) ?
C8 C7 C4 109.47(16) ?
C9 C7 C4 110.04(15) ?
C10 C7 C4 111.54(14) ?
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
H8A C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
H8A C8 H8C 109.5 ?
H8B C8 H8C 109.5 ?
C7 C9 H9A 109.5 ?
C7 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
C7 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
C7 C10 H10A 109.5 ?
C7 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
C7 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
O1 C11 C12 127.51(14) ?
O1 C11 C16 117.45(13) ?
C12 C11 C16 114.98(14) ?
C13 C12 C11 122.12(14) ?
C13 C12 N1 116.36(14) ?
C11 C12 N1 121.36(14) ?
C14 C13 C12 119.12(15) ?
C14 C13 H13 120.4 ?
C12 C13 H13 120.4 ?
C13 C14 C15 122.06(15) ?
C13 C14 N2 119.03(15) ?
C15 C14 N2 118.90(15) ?
C16 C15 C14 116.89(15) ?
C16 C15 H15 121.6 ?
C14 C15 H15 121.6 ?
C15 C16 C11 124.77(14) ?
C15 C16 N3 117.93(14) ?
C11 C16 N3 117.30(13) ?
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
O1 C11 . 1.3383(19) y
O1 C1 . 1.4964(18) y
O2 N1 . 1.2259(18) y
O3 N1 . 1.2281(17) y
O4 N2 . 1.217(2) y
O5 N2 . 1.228(2) y
O6 N3 . 1.2052(19) y
O7 N3 . 1.2103(18) y
N1 C12 . 1.467(2) y
N2 C14 . 1.471(2) y
N3 C16 . 1.471(2) y
C1 C6 . 1.507(2) y
C1 C2 . 1.508(3) y
C1 H1 . 1.0000 ?
C2 C3 . 1.522(2) y
C2 H2A . .9900 ?
C2 H2B . .9900 ?
C3 C4 . 1.532(2) y
C3 H3A . .9900 ?
C3 H3B . .9900 ?
C4 C5 . 1.535(3) y
C4 C7 . 1.553(2) y
C4 H4 . 1.0000 ?
C5 C6 . 1.529(2) y
C5 H5A . .9900 ?
C5 H5B . .9900 ?
C6 H6A . .9900 ?
C6 H6B . .9900 ?
C7 C8 . 1.526(3) y
C7 C9 . 1.534(3) y
C7 C10 . 1.541(2) y
C8 H8A . .9800 ?
C8 H8B . .9800 ?
C8 H8C . .9800 ?
C9 H9A . .9800 ?
C9 H9B . .9800 ?
C9 H9C . .9800 ?
C10 H10A . .9800 ?
C10 H10B . .9800 ?
C10 H10C . .9800 ?
C11 C12 . 1.403(2) y
C11 C16 . 1.404(2) y
C12 C13 . 1.384(2) y
C13 C14 . 1.378(2) y
C13 H13 . .9500 ?
C14 C15 . 1.380(2) ?
C15 C16 . 1.375(2) ?
C15 H15 . .9500 ?
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
_geom_torsion_publ_flag
C11 O1 C1 C6 155.11(14) y
C11 O1 C1 C2 -83.98(17) y
O1 C1 C2 C3 -67.89(17) y
C6 C1 C2 C3 48.26(19) ?
C1 C2 C3 C4 -50.75(19) ?
C2 C3 C4 C5 54.79(18) ?
C2 C3 C4 C7 -177.32(14) ?
C3 C4 C5 C6 -58.41(17) ?
C7 C4 C5 C6 174.06(14) ?
O1 C1 C6 C5 66.86(17) y
C2 C1 C6 C5 -51.34(18) ?
C4 C5 C6 C1 57.57(18) ?
C3 C4 C7 C8 170.95(18) ?
C5 C4 C7 C8 -64.0(2) ?
C3 C4 C7 C9 52.85(18) ?
C5 C4 C7 C9 177.87(14) ?
C3 C4 C7 C10 -67.1(2) ?
C5 C4 C7 C10 57.9(2) ?
C1 O1 C11 C12 -56.7(2) y
C1 O1 C11 C16 126.24(15) y
O1 C11 C12 C13 -178.53(15) ?
C16 C11 C12 C13 -1.4(2) ?
O1 C11 C12 N1 -3.4(2) ?
C16 C11 C12 N1 173.79(13) ?
O2 N1 C12 C13 144.63(15) y
O3 N1 C12 C13 -32.9(2) y
O2 N1 C12 C11 -30.8(2) y
O3 N1 C12 C11 151.64(14) y
C11 C12 C13 C14 2.7(2) ?
N1 C12 C13 C14 -172.67(14) ?
C12 C13 C14 C15 -1.8(2) ?
C12 C13 C14 N2 177.30(14) ?
O4 N2 C14 C13 12.2(3) y
O5 N2 C14 C13 -167.98(16) y
O4 N2 C14 C15 -168.67(17) y
O5 N2 C14 C15 11.2(2) y
C13 C14 C15 C16 -.3(2) ?
N2 C14 C15 C16 -179.46(14) ?
C14 C15 C16 C11 1.8(2) ?
C14 C15 C16 N3 -177.76(14) ?
O1 C11 C16 C15 176.52(14) ?
C12 C11 C16 C15 -.9(2) ?
O1 C11 C16 N3 -3.9(2) ?
C12 C11 C16 N3 178.61(13) ?
O6 N3 C16 C15 -104.03(19) y
O7 N3 C16 C15 75.94(18) y
O6 N3 C16 C11 76.4(2) y
O7 N3 C16 C11 -103.64(17) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21107400
