#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:34:17 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229131 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/13/7231327.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_7231327
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                   14.205(4)
_cell_length_b                   14.205(4)
_cell_length_c                   6.6233(18)
_cell_measurement_reflns_used    732
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      16.98
_cell_measurement_theta_min      2.87
_cell_volume                     1157.4(6)
_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 0.911
_diffrn_measured_fraction_theta_max 0.911
_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  0.0641
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.911
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5148
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        24.951
_diffrn_reflns_theta_max         24.951
_diffrn_reflns_theta_min         3.312
_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    0.940
_exptl_crystal_description       needle
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.995
_exptl_transmission_factor_min   0.991
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 221 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         1262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0718
_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)+(0.0876P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1868
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                718
_reflns_number_total             1262
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01169a3.cif
_cod_data_source_block           1_CCl4
_cod_depositor_comments
'Adding full bibliography for 7231324--7231340.cif.'
_cod_original_cell_volume        1157.4(7)
_cod_database_code               7231327
_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   0.968
_shelx_estimated_absorpt_t_max   0.995
_platon_squeeze_void_probe_radius 1.20
_shelx_res_file
;
TITL xm in P3(2)21
    F:\Manuscript\NTE_dd026_VT\dd026_solvates\dd026ccl4\work\XM.res
    created by SHELXL-2018/3 at 21:53:22 on 04-Apr-2018
CELL 0.71073 14.2050 14.2050 6.6233 90.000 90.000 120.000
ZERR 3.0000 0.0039 0.0039 0.0018 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
OMIT 0 1 0
OMIT -1 2 0
OMIT 1 1 0
OMIT 0 4 0
OMIT -2 2 1
ACTA 50
FMAP 2 1 53
GRID
PLAN 5 0 0
MERG 2
SIZE 0.53 0.13 0.08
TEMP -173
L.S. 100
WGHT    0.087600
FVAR       4.01490
O1    3    0.273056    0.678765    0.009252    11.00000    0.08095    0.08257 =
         0.04521   -0.00656   -0.01181    0.04590
H1    2    0.304807    0.680100    0.103596    11.00000    0.04152
C1    1    0.210459    0.731133    0.014586    11.00000    0.07751    0.06869 =
         0.04644    0.01383    0.01024    0.02852
C2    1    0.280013    0.851131    0.066454    11.00000    0.09041    0.06503 =
         0.07928    0.00143   -0.00048    0.03751
AFIX  23
H2A   2    0.234663    0.880515    0.119187    11.00000   -1.20000
H2B   2    0.335745    0.862667    0.168434    11.00000   -1.20000
AFIX   0
C3    1    0.330316    0.902216   -0.124082    11.00000    0.15647    0.11539 =
         0.09201    0.02096   -0.00672    0.03853
AFIX  23
H3B   2    0.404064    0.911554   -0.133661    11.00000   -1.20000
H3A   2    0.336556    0.974650   -0.134510    11.00000   -1.20000
AFIX   0
C4    1    0.260070    0.830057   -0.288643    11.00000    0.14553    0.14021 =
         0.11003    0.04495    0.01852    0.06707
AFIX  23
H4A   2    0.228801    0.867252   -0.366944    11.00000   -1.20000
H4B   2    0.303596    0.812285   -0.381470    11.00000   -1.20000
AFIX   0
C5    1    0.171989    0.729403   -0.197456    11.00000    0.07158    0.09451 =
         0.06142    0.01293   -0.00531    0.04083
AFIX  23
H5B   2    0.161982    0.664403   -0.271208    11.00000   -1.20000
H5A   2    0.102481    0.729772   -0.197847    11.00000   -1.20000
AFIX   0
C6    1    0.121499    0.676312    0.158692    11.00000    0.08963    0.07432 =
         0.07030   -0.01313   -0.02283    0.04878
C7    1    0.042382    0.636729    0.270942    11.00000    0.06675    0.07756 =
         0.06423   -0.00207    0.00173    0.01958
HKLF 4




REM  xm in P3(2)21
REM wR2 = 0.1868, GooF = S = 0.943, Restrained GooF = 0.943 for all data
REM R1 = 0.0718 for 718 Fo > 4sig(Fo) and 0.1262 for all 1262 data
REM 77 parameters refined using 0 restraints

END

WGHT      0.0876      0.0000

REM Highest difference peak  0.156,  deepest hole -0.136,  1-sigma level  0.035
Q1    1   0.1746  0.8272 -0.2065  11.00000  0.05    0.16
Q2    1   0.2670  0.7726  0.1143  11.00000  0.05    0.13
Q3    1   0.2445  0.8849 -0.0232  11.00000  0.05    0.13
Q4    1   0.0000  0.6850  0.3333  10.50000  0.05    0.12
Q5    1   0.1980  0.7458  0.2359  11.00000  0.05    0.11
;
_shelx_res_checksum              51247
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 0.2731(3) 0.6788(3) 0.0093(6) 0.0673(12) Uani 1 1 d . .
H1 H 0.305(4) 0.680(4) 0.104(8) 0.042(15) Uiso 1 1 d . .
C1 C 0.2105(5) 0.7311(5) 0.0146(8) 0.0678(16) Uani 1 1 d . .
C2 C 0.2800(6) 0.8511(5) 0.0665(9) 0.0788(19) Uani 1 1 d . .
H2A H 0.234663 0.880515 0.119187 0.095 Uiso 1 1 calc R U
H2B H 0.335745 0.862667 0.168434 0.095 Uiso 1 1 calc R U
C3 C 0.3303(9) 0.9022(8) -0.1241(13) 0.134(4) Uani 1 1 d . .
H3B H 0.404064 0.911554 -0.133661 0.161 Uiso 1 1 calc R U
H3A H 0.336556 0.974650 -0.134510 0.161 Uiso 1 1 calc R U
C4 C 0.2601(10) 0.8301(9) -0.2886(17) 0.134(4) Uani 1 1 d . .
H4A H 0.228801 0.867252 -0.366944 0.161 Uiso 1 1 calc R U
H4B H 0.303596 0.812285 -0.381470 0.161 Uiso 1 1 calc R U
C5 C 0.1720(5) 0.7294(5) -0.1975(9) 0.0761(18) Uani 1 1 d . .
H5B H 0.161982 0.664403 -0.271208 0.091 Uiso 1 1 calc R U
H5A H 0.102481 0.729772 -0.197847 0.091 Uiso 1 1 calc R U
C6 C 0.1215(6) 0.6763(5) 0.1587(10) 0.0746(18) Uani 1 1 d . .
C7 C 0.0424(5) 0.6367(6) 0.2709(10) 0.0768(18) 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 0.081(3) 0.083(3) 0.045(2) -0.0066(19) -0.012(2) 0.046(2)
C1 0.078(4) 0.069(4) 0.046(3) 0.014(3) 0.010(3) 0.029(3)
C2 0.090(5) 0.065(4) 0.079(5) 0.001(4) 0.000(4) 0.038(4)
C3 0.156(9) 0.115(7) 0.092(6) 0.021(5) -0.007(6) 0.039(6)
C4 0.146(8) 0.140(8) 0.110(7) 0.045(6) 0.019(6) 0.067(7)
C5 0.072(4) 0.095(5) 0.061(4) 0.013(3) -0.005(3) 0.041(3)
C6 0.090(5) 0.074(4) 0.070(4) -0.013(4) -0.023(4) 0.049(4)
C7 0.067(4) 0.078(4) 0.064(4) -0.002(3) 0.002(3) 0.020(3)
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 119(3) .
O1 C1 C6 109.8(5) .
O1 C1 C5 106.7(5) .
C6 C1 C5 113.1(5) .
O1 C1 C2 111.6(5) .
C6 C1 C2 110.7(5) .
C5 C1 C2 104.9(5) .
C3 C2 C1 104.2(6) .
C3 C2 H2A 110.9 .
C1 C2 H2A 110.9 .
C3 C2 H2B 110.9 .
C1 C2 H2B 110.9 .
H2A C2 H2B 108.9 .
C2 C3 C4 107.4(8) .
C2 C3 H3B 110.2 .
C4 C3 H3B 110.2 .
C2 C3 H3A 110.2 .
C4 C3 H3A 110.2 .
H3B C3 H3A 108.5 .
C5 C4 C3 108.6(8) .
C5 C4 H4A 110.0 .
C3 C4 H4A 110.0 .
C5 C4 H4B 110.0 .
C3 C4 H4B 110.0 .
H4A C4 H4B 108.4 .
C4 C5 C1 103.9(7) .
C4 C5 H5B 111.0 .
C1 C5 H5B 111.0 .
C4 C5 H5A 111.0 .
C1 C5 H5A 111.0 .
H5B C5 H5A 109.0 .
C7 C6 C1 173.1(7) .
C6 C7 C7 179.0(9) 5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.417(8) .
O1 H1 0.77(5) .
C1 C6 1.460(10) .
C1 C5 1.503(8) .
C1 C2 1.522(10) .
C2 C3 1.453(11) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.487(14) .
C3 H3B 0.9900 .
C3 H3A 0.9900 .
C4 C5 1.478(12) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 H5B 0.9900 .
C5 H5A 0.9900 .
C6 C7 1.225(9) .
C7 C7 1.331(14) 5
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
_platon_squeeze_void_content
1 0.000 0.000 -0.032 301 94 ' '
