#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:34:17 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229131 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/13/7231326.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_7231326
loop_
_publ_author_name
'Das, Dinabandhu'
'Barbour, Leonard J.'
_publ_section_title
;
 Uniaxial negative thermal expansion induced by moiety twisting in an
 organic crystal
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              5123
_journal_paper_doi               10.1039/C8CE01169A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C14 H18 O2'
_chemical_formula_weight         218.28
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_symmetry_space_group_name_Hall  'P 32 2"'
_symmetry_space_group_name_H-M   'P 32 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-07-12 deposited with the CCDC.
2018-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   14.3565(5)
_cell_length_b                   14.3565(5)
_cell_length_c                   6.5749(2)
_cell_measurement_reflns_used    2884
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.92
_cell_measurement_theta_min      2.84
_cell_volume                     1173.59(7)
_computing_cell_refinement       'Bruker SMART APEX-II'
_computing_data_collection       'Bruker SMART APEX-II'
_computing_data_reduction        'Bruker SAINT '
_computing_molecular_graphics    'XSEED (Barbour 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8288
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        23.378
_diffrn_reflns_theta_max         23.378
_diffrn_reflns_theta_min         1.638
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.927
_exptl_crystal_description       needle
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_exptl_transmission_factor_max   0.993
_exptl_transmission_factor_min   0.986
_platon_squeeze_details          ' ?'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 441 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1148
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0825P)²+0.3376P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1071
_reflns_number_total             1148
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01169a3.cif
_cod_data_source_block           1_EtOAc
_cod_depositor_comments
'Adding full bibliography for 7231324--7231340.cif.'
_cod_original_cell_volume        1173.59(9)
_cod_database_code               7231326
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_file
;
TITL xm in P3(2)21
    F:\Manuscript\NTE_dd026_VT\dd026_solvates\work_dd026_EtOAc\DD026et.res
    created by SHELXL-2018/3 at 22:33:22 on 04-Apr-2018
CELL 0.71073 14.3565 14.3565 6.5749 90.000 90.000 120.000
ZERR 3.0000 0.0005 0.0005 0.0002 0.000 0.000 0.000
LATT -1
SYMM -Y, X-Y, 0.666667+Z
SYMM -X+Y, -X, 0.333333+Z
SYMM X-Y, -Y, 0.333333-Z
SYMM -X, -X+Y, 0.666667-Z
SYMM Y, X, -Z
SFAC C H O
UNIT 42 54 6
BOND $H
ACTA 50
FMAP 2 1 53
GRID
PLAN 5 0 0
SIZE 0.67 0.19 0.11
TEMP -173
L.S. 100
WGHT    0.082500    0.337600
FVAR       4.01394
O1    3    0.679702    0.275716   -0.008391    11.00000    0.04690    0.03800 =
         0.01512    0.00098    0.00179    0.02415
H1    2    0.681825    0.308345   -0.111102    11.00000    0.06365
C1    1    0.729861    0.211284   -0.018744    11.00000    0.03856    0.03747 =
         0.01724   -0.00199   -0.00219    0.01946
C2    1    0.849181    0.279996   -0.068729    11.00000    0.03790    0.04487 =
         0.03029   -0.00491   -0.00316    0.01782
AFIX  23
H2A   2    0.878261    0.234733   -0.119690    11.00000   -1.20000
H2B   2    0.861038    0.334567   -0.173074    11.00000   -1.20000
AFIX   0
C3    1    0.902412    0.333597    0.131231    11.00000    0.05463    0.06112 =
         0.03406   -0.00263   -0.01153    0.01126
AFIX  23
H3A   2    0.971568    0.334800    0.147338    11.00000   -1.20000
H3B   2    0.916680    0.408557    0.134470    11.00000   -1.20000
AFIX   0
C4    1    0.825175    0.268085    0.300905    11.00000    0.05507    0.06514 =
         0.03139   -0.01294   -0.01268    0.03010
AFIX  23
H4B   2    0.800348    0.311797    0.374725    11.00000   -1.20000
H4A   2    0.860860    0.243645    0.398857    11.00000   -1.20000
AFIX   0
C5    1    0.730693    0.172029    0.199005    11.00000    0.05170    0.04089 =
         0.01967    0.00132   -0.00304    0.02516
AFIX  23
H5B   2    0.662498    0.152197    0.270225    11.00000   -1.20000
H5A   2    0.741361    0.109031    0.197403    11.00000   -1.20000
AFIX   0
C6    1    0.672653    0.121632   -0.158601    11.00000    0.03941    0.03874 =
         0.02374    0.00083    0.00089    0.02174
C7    1    0.630841    0.044357   -0.271018    11.00000    0.04412    0.03724 =
         0.02339   -0.00138   -0.00069    0.01981
HKLF 4




REM  xm in P3(2)21
REM wR2 = 0.1365, GooF = S = 1.104, Restrained GooF = 1.104 for all data
REM R1 = 0.0497 for 1071 Fo > 4sig(Fo) and 0.0528 for all 1148 data
REM 77 parameters refined using 0 restraints

END

WGHT      0.0825      0.3366

REM Highest difference peak  0.208,  deepest hole -0.191,  1-sigma level  0.048
Q1    1   0.8694  0.0350  0.5731  11.00000  0.05    0.21
Q2    1   0.8024 -0.0006 -0.2916  11.00000  0.05    0.16
Q3    1   0.8024  0.3609 -0.2968  11.00000  0.05    0.16
Q4    1   0.9451  0.0737 -0.0868  11.00000  0.05    0.15
Q5    1   0.5977  0.1032 -0.1162  11.00000  0.05    0.15
;
_shelx_res_checksum              41872
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.6797(2) 0.27572(19) -0.0084(4) 0.0320(7) Uani 1 1 d . .
H1 H 0.682(4) 0.308(4) -0.111(9) 0.064(15) Uiso 1 1 d . .
C1 C 0.7299(3) 0.2113(3) -0.0187(5) 0.0309(9) Uani 1 1 d . .
C2 C 0.8492(3) 0.2800(3) -0.0687(5) 0.0390(9) Uani 1 1 d . .
H2A H 0.878261 0.234733 -0.119690 0.047 Uiso 1 1 calc R U
H2B H 0.861038 0.334567 -0.173074 0.047 Uiso 1 1 calc R U
C3 C 0.9024(4) 0.3336(4) 0.1312(6) 0.0578(13) Uani 1 1 d . .
H3A H 0.971568 0.334800 0.147338 0.069 Uiso 1 1 calc R U
H3B H 0.916680 0.408557 0.134470 0.069 Uiso 1 1 calc R U
C4 C 0.8252(4) 0.2681(4) 0.3009(6) 0.0505(11) Uani 1 1 d . .
H4B H 0.800348 0.311797 0.374725 0.061 Uiso 1 1 calc R U
H4A H 0.860860 0.243645 0.398857 0.061 Uiso 1 1 calc R U
C5 C 0.7307(3) 0.1720(3) 0.1990(5) 0.0365(10) Uani 1 1 d . .
H5B H 0.662498 0.152197 0.270225 0.044 Uiso 1 1 calc R U
H5A H 0.741361 0.109031 0.197403 0.044 Uiso 1 1 calc R U
C6 C 0.6727(3) 0.1216(3) -0.1586(5) 0.0330(9) Uani 1 1 d . .
C7 C 0.6308(3) 0.0444(3) -0.2710(5) 0.0351(9) Uani 1 1 d . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0469(16) 0.0380(14) 0.0151(12) 0.0010(10) 0.0018(10) 0.0241(12)
C1 0.039(2) 0.037(2) 0.0172(16) -0.0020(14) -0.0022(14) 0.0195(17)
C2 0.038(2) 0.045(2) 0.0303(19) -0.0049(17) -0.0032(16) 0.0178(19)
C3 0.055(3) 0.061(3) 0.034(2) -0.0026(19) -0.012(2) 0.011(2)
C4 0.055(3) 0.065(3) 0.0314(19) -0.0129(19) -0.013(2) 0.030(2)
C5 0.052(2) 0.041(2) 0.0197(17) 0.0013(15) -0.0030(16) 0.0252(18)
C6 0.039(2) 0.039(2) 0.0237(17) 0.0008(16) 0.0009(15) 0.0217(18)
C7 0.044(2) 0.037(2) 0.0234(17) -0.0014(14) -0.0007(15) 0.0198(18)
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'
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
C1 O1 H1 117(3) .
O1 C1 C6 111.0(3) .
O1 C1 C2 111.0(3) .
C6 C1 C2 113.0(3) .
O1 C1 C5 106.9(3) .
C6 C1 C5 111.6(3) .
C2 C1 C5 103.0(3) .
C3 C2 C1 105.0(3) .
C3 C2 H2A 110.8 .
C1 C2 H2A 110.8 .
C3 C2 H2B 110.8 .
C1 C2 H2B 110.8 .
H2A C2 H2B 108.8 .
C4 C3 C2 107.1(3) .
C4 C3 H3A 110.3 .
C2 C3 H3A 110.3 .
C4 C3 H3B 110.3 .
C2 C3 H3B 110.3 .
H3A C3 H3B 108.5 .
C3 C4 C5 106.3(3) .
C3 C4 H4B 110.5 .
C5 C4 H4B 110.5 .
C3 C4 H4A 110.5 .
C5 C4 H4A 110.5 .
H4B C4 H4A 108.7 .
C4 C5 C1 104.1(3) .
C4 C5 H5B 110.9 .
C1 C5 H5B 110.9 .
C4 C5 H5A 110.9 .
C1 C5 H5A 110.9 .
H5B C5 H5A 109.0 .
C7 C6 C1 174.8(4) .
C6 C7 C7 177.6(3) 4_554
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.430(4) .
O1 H1 0.81(6) .
C1 C6 1.456(5) .
C1 C2 1.525(5) .
C1 C5 1.541(5) .
C2 C3 1.522(6) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.522(6) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.523(6) .
C4 H4B 0.9900 .
C4 H4A 0.9900 .
C5 H5B 0.9900 .
C5 H5A 0.9900 .
C6 C7 1.213(5) .
C7 C7 1.374(7) 4_554
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.000 -0.032 310.0 90.7
