#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:34:17 +0100 (dom 17 de nov de 2019) $
#$Revision: 229131 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/13/7231334.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_7231334
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            'C10.5 H13.5 N0 O1.5'
_chemical_formula_weight         163.71
_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   geom
_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            4
_cell_length_a                   14.250(7)
_cell_length_b                   14.250(7)
_cell_length_c                   6.620(7)
_cell_measurement_reflns_used    365
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      13.20
_cell_measurement_theta_min      2.86
_cell_volume                     1164.2(15)
_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 1.000
_diffrn_measured_fraction_theta_max 0.967
_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  0.1239
_diffrn_reflns_av_unetI/netI     0.1471
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7074
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.493
_diffrn_reflns_theta_min         1.650
_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    0.934
_exptl_crystal_description       needle
_exptl_crystal_F_000             354
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_transmission_factor_max   0.999
_exptl_transmission_factor_min   0.999
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.838
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.838
_refine_ls_R_factor_all          0.2045
_refine_ls_R_factor_gt           0.0835
_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)+(0.1211P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2036
_refine_ls_wR_factor_ref         0.2461
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.918
_reflns_number_gt                650
_reflns_number_total             1868
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01169a3.cif
_cod_data_source_block           1_CHCl3
_cod_depositor_comments
'Adding full bibliography for 7231324--7231340.cif.'
_cod_original_cell_volume        1164.2(17)
_cod_original_formula_sum        'C10.50 H13.50 N0 O1.50'
_cod_database_code               7231334
_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   0.993
_shelx_estimated_absorpt_t_max   0.999
_platon_squeeze_void_probe_radius 1.20
_shelx_res_file
;
TITL xm in P3(2)
    F:\Manuscript\NTE_dd026_VT\dd026_solvates\dd026_CHCl3\work\XM.res
    created by SHELXL-2018/3 at 21:36:26 on 04-Apr-2018
CELL 0.71073 14.2505 14.2505 6.6195 90.000 90.000 120.000
ZERR 4.0000 0.0073 0.0073 0.0066 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 N
UNIT 42 54 6 0
BOND
ACTA 50
FMAP 2 1 53
GRID
PLAN 5 0 0
MERG 2
SIZE 0.12 0.02 0.02
TEMP -100
L.S. 100
WGHT    0.121100
FVAR      14.34626
O1    3    0.274158    0.595381    0.155913    11.00000    0.08716    0.07617 =
         0.05248   -0.00417    0.00642    0.04043
AFIX 147
H1    2    0.305290    0.618256    0.044170    11.00000   -1.20000
AFIX   0
C1    1    0.211291    0.480459    0.150971    11.00000    0.08119    0.08265 =
         0.04142    0.00540    0.00048    0.03948
C2    1    0.282424    0.430876    0.100022    11.00000    0.11656    0.11145 =
         0.07469   -0.00787    0.01653    0.07601
AFIX  23
H2A   2    0.237761    0.357526    0.041965    11.00000   -1.20000
H2B   2    0.338727    0.476629    0.000458    11.00000   -1.20000
AFIX   0
C3    1    0.332550    0.425210    0.288405    11.00000    0.14875    0.24826 =
         0.09598    0.02234   -0.01477    0.11836
AFIX  23
H3B   2    0.407975    0.486075    0.298830    11.00000   -1.20000
H3A   2    0.332759    0.356002    0.298493    11.00000   -1.20000
AFIX   0
C4    1    0.259494    0.433122    0.455704    11.00000    0.17836    0.16667 =
         0.10852    0.02067    0.00066    0.09566
AFIX  23
H4A   2    0.228873    0.367575    0.541798    11.00000   -1.20000
H4B   2    0.303770    0.496935    0.542330    11.00000   -1.20000
AFIX   0
C5    1    0.170640    0.443115    0.363135    11.00000    0.06679    0.13536 =
         0.06155    0.00681   -0.00674    0.04742
AFIX  23
H5B   2    0.158791    0.497078    0.435645    11.00000   -1.20000
H5A   2    0.102246    0.372617    0.362227    11.00000   -1.20000
AFIX   0
C6    1    0.119371    0.444560    0.007696    11.00000    0.05689    0.08610 =
         0.07517    0.00047    0.00469    0.04347
C7    1    0.041742    0.406518   -0.104075    11.00000    0.05872    0.10027 =
         0.08217    0.00938    0.00009    0.04010
HKLF 4




REM  xm in P3(2)
REM wR2 = 0.2461, GooF = S = 0.838, Restrained GooF = 0.838 for all data
REM R1 = 0.0835 for 650 Fo > 4sig(Fo) and 0.2045 for all 1868 data
REM 74 parameters refined using 0 restraints

END

WGHT      0.1211      0.0000

REM Highest difference peak  0.200,  deepest hole -0.197,  1-sigma level  0.049
Q1    1   0.1689  0.3425  0.3919  11.00000  0.05    0.20
Q2    1   0.1799  0.4482 -0.0396  11.00000  0.05    0.14
Q3    1   0.3145  0.5886  0.4786  11.00000  0.05    0.14
Q4    1   0.1934  0.5135  0.2579  11.00000  0.05    0.13
Q5    1   0.3644  0.3644  0.0000  10.50000  0.05    0.13
;
_shelx_res_checksum              38747
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 0.2742(3) 0.5954(3) 0.1559(5) 0.0721(13) Uani 1 1 d . .
H1 H 0.305290 0.618256 0.044170 0.087 Uiso 1 1 calc R U
C1 C 0.2113(5) 0.4805(5) 0.1510(7) 0.0691(16) Uani 1 1 d . .
C2 C 0.2824(7) 0.4309(6) 0.1000(9) 0.092(2) Uani 1 1 d . .
H2A H 0.237761 0.357526 0.041965 0.111 Uiso 1 1 calc R U
H2B H 0.338727 0.476629 0.000458 0.111 Uiso 1 1 calc R U
C3 C 0.3325(9) 0.4252(11) 0.2884(12) 0.156(5) Uani 1 1 d . .
H3B H 0.407975 0.486075 0.298830 0.187 Uiso 1 1 calc R U
H3A H 0.332759 0.356002 0.298493 0.187 Uiso 1 1 calc R U
C4 C 0.2595(11) 0.4331(10) 0.4557(13) 0.147(4) Uani 1 1 d . .
H4A H 0.228873 0.367575 0.541798 0.176 Uiso 1 1 calc R U
H4B H 0.303770 0.496935 0.542330 0.176 Uiso 1 1 calc R U
C5 C 0.1706(5) 0.4431(6) 0.3631(8) 0.089(2) Uani 1 1 d . .
H5B H 0.158791 0.497078 0.435645 0.107 Uiso 1 1 calc R U
H5A H 0.102246 0.372617 0.362227 0.107 Uiso 1 1 calc R U
C6 C 0.1194(5) 0.4446(5) 0.0077(8) 0.0693(16) Uani 1 1 d . .
C7 C 0.0417(5) 0.4065(6) -0.1041(9) 0.0802(19) 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 0.087(3) 0.076(3) 0.052(2) -0.0042(18) 0.006(2) 0.040(3)
C1 0.081(4) 0.083(4) 0.041(3) 0.005(3) 0.000(3) 0.039(4)
C2 0.117(6) 0.111(6) 0.075(4) -0.008(4) 0.017(4) 0.076(5)
C3 0.149(9) 0.248(14) 0.096(6) 0.022(7) -0.015(6) 0.118(9)
C4 0.178(10) 0.167(9) 0.109(6) 0.021(6) 0.001(7) 0.096(8)
C5 0.067(4) 0.135(6) 0.062(4) 0.007(4) -0.007(3) 0.047(4)
C6 0.057(4) 0.086(5) 0.075(4) 0.000(3) 0.005(4) 0.043(4)
C7 0.059(4) 0.100(5) 0.082(5) 0.009(4) 0.000(3) 0.040(4)
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'
N N 0.0061 0.0033 '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
O1 C1 C6 110.5(5) .
O1 C1 C5 107.1(5) .
C6 C1 C5 110.8(5) .
O1 C1 C2 110.8(5) .
C6 C1 C2 111.9(5) .
C5 C1 C2 105.5(5) .
C3 C2 C1 107.0(5) .
C2 C3 C4 103.9(8) .
C5 C4 C3 110.3(7) .
C4 C5 C1 102.9(6) .
C7 C6 C1 174.5(7) .
C6 C7 C7 178.8(8) 5_554
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.421(7) .
C1 C6 1.486(8) .
C1 C5 1.511(8) .
C1 C2 1.535(10) .
C2 C3 1.459(10) .
C3 C4 1.562(14) .
C4 C5 1.476(12) .
C6 C7 1.211(7) .
C7 C7 1.322(13) 5_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
_platon_squeeze_void_content
1 0.000 0.000 -0.034 300 103 ' '
