#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:20:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180473 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/42/7214279.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_7214279
loop_
_publ_author_name
'Bhattacharya, Suman'
'Saha, Binoy K.'
_publ_section_title
;
 Steric guided anomalous thermal expansion in a dimorphic organic system
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              2340
_journal_paper_doi               10.1039/c3ce41869c
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C17 H22 N2'
_chemical_formula_sum            'C17 H22 N2'
_chemical_formula_weight         254.37
_chemical_name_common            MBDA-Form-II
_chemical_name_systematic
;
4,4'-Methylene-bis(2,6-dimethylaniline)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-22
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr  9 2013 14:06:00, GUI svn.r4458)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 132.931(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.6512(18)
_cell_length_b                   8.1468(5)
_cell_length_c                   14.2338(10)
_cell_measurement_reflns_used    786
_cell_measurement_temperature    268(2)
_cell_measurement_theta_max      29.0707
_cell_measurement_theta_min      4.4478
_cell_volume                     1498.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      268(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3724
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         4.46
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         3909
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0545P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                949
_reflns_number_total             1728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41869c3.cif
_cod_data_source_block           MBDA-Form-II-268
_cod_original_cell_volume        1498.6(2)
_cod_database_code               7214279
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C9 C 0.0000 0.1437(3) 0.2500 0.0568(6) Uani 1 2 d S
H9A H 0.0259 0.2139 0.3216 0.068 Uiso 0.50 1 calc PR
H9B H -0.0259 0.2139 0.1784 0.068 Uiso 0.50 1 calc PR
C5 C 0.18422(14) 0.03528(18) 0.41081(16) 0.0525(5) Uani 1 1 d .
H5 H 0.1952 0.0988 0.4735 0.063 Uiso 1 1 calc R
C2 C 0.15190(13) -0.15415(19) 0.22562(16) 0.0509(4) Uani 1 1 d .
C4 C 0.08848(13) 0.04186(17) 0.28673(16) 0.0470(4) Uani 1 1 d .
C3 C 0.07519(13) -0.05402(18) 0.19598(15) 0.0488(4) Uani 1 1 d .
H3 H 0.0118 -0.0506 0.1115 0.059 Uiso 1 1 calc R
C1 C 0.24770(14) -0.15802(19) 0.35185(18) 0.0536(5) Uani 1 1 d .
C6 C 0.26459(13) -0.0621(2) 0.44582(16) 0.0528(5) Uani 1 1 d .
N1 N 0.32801(17) -0.2551(3) 0.3843(3) 0.0845(6) Uani 1 1 d .
C8 C 0.13241(16) -0.2619(3) 0.12457(18) 0.0799(7) Uani 1 1 d .
H8A H 0.1357 -0.3752 0.1457 0.120 Uiso 1 1 calc R
H8B H 0.1841 -0.2406 0.1213 0.120 Uiso 1 1 calc R
H8C H 0.0651 -0.2385 0.0425 0.120 Uiso 1 1 calc R
C7 C 0.36755(15) -0.0633(3) 0.58168(18) 0.0779(6) Uani 1 1 d .
H7A H 0.4201 -0.0254 0.5836 0.117 Uiso 1 1 calc R
H7B H 0.3835 -0.1730 0.6151 0.117 Uiso 1 1 calc R
H7C H 0.3648 0.0077 0.6332 0.117 Uiso 1 1 calc R
H1A H 0.311(2) -0.321(4) 0.322(3) 0.162(14) Uiso 1 1 d .
H1B H 0.3787(18) -0.272(3) 0.465(2) 0.105(9) Uiso 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
C9 0.0769(18) 0.0330(11) 0.0813(16) 0.000 0.0620(16) 0.000
C5 0.0715(13) 0.0410(8) 0.0618(11) -0.0110(8) 0.0520(11) -0.0174(9)
C2 0.0648(12) 0.0442(9) 0.0612(10) 0.0040(8) 0.0498(10) 0.0039(9)
C4 0.0612(11) 0.0329(7) 0.0648(11) -0.0017(8) 0.0500(10) -0.0064(8)
C3 0.0581(11) 0.0422(8) 0.0548(9) 0.0008(8) 0.0418(9) -0.0014(8)
C1 0.0591(11) 0.0436(9) 0.0741(12) 0.0090(9) 0.0517(11) 0.0036(9)
C6 0.0558(11) 0.0441(9) 0.0602(11) 0.0043(8) 0.0402(10) -0.0092(9)
N1 0.0767(14) 0.0840(13) 0.0976(16) 0.0162(13) 0.0613(14) 0.0238(12)
C8 0.1055(17) 0.0782(14) 0.0835(14) -0.0021(11) 0.0752(14) 0.0176(13)
C7 0.0702(14) 0.0718(13) 0.0710(12) 0.0033(11) 0.0400(12) -0.0173(12)
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'
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_1
H9A C9 H9B 107.7 .
C4 C9 H9A 108.9 2
C4 C9 H9A 108.9 .
C4 C9 H9B 108.9 2
C4 C9 H9B 108.9 .
C4 C9 C4 113.48(17) 2
C4 C5 H5 118.6 .
C4 C5 C6 122.80(15) .
C6 C5 H5 118.6 .
C3 C2 C1 118.91(15) .
C3 C2 C8 120.89(16) .
C1 C2 C8 120.18(15) .
C5 C4 C9 122.58(13) .
C5 C4 C3 116.89(15) .
C3 C4 C9 120.50(14) .
C2 C3 C4 122.76(16) .
C2 C3 H3 118.6 .
C4 C3 H3 118.6 .
C2 C1 N1 120.28(18) .
C6 C1 C2 120.13(15) .
C6 C1 N1 119.6(2) .
C5 C6 C1 118.51(16) .
C5 C6 C7 120.69(16) .
C1 C6 C7 120.80(17) .
C1 N1 H1A 115(2) .
C1 N1 H1B 115.3(16) .
H1A N1 H1B 125(3) .
C2 C8 H8A 109.5 .
C2 C8 H8B 109.5 .
C2 C8 H8C 109.5 .
H8A C8 H8B 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C6 C7 H7A 109.5 .
C6 C7 H7B 109.5 .
C6 C7 H7C 109.5 .
H7A C7 H7B 109.5 .
H7A C7 H7C 109.5 .
H7B C7 H7C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C4 1.5127(19) 2
C9 C4 1.5128(19) .
C5 H5 0.9300 .
C5 C4 1.383(2) .
C5 C6 1.388(2) .
C2 C3 1.378(2) .
C2 C1 1.396(2) .
C2 C8 1.511(2) .
C4 C3 1.386(2) .
C3 H3 0.9300 .
C1 C6 1.395(2) .
C1 N1 1.399(2) .
C6 C7 1.502(2) .
N1 H1A 0.89(3) .
N1 H1B 0.86(2) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
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_site_symmetry_1
C9 C4 C3 C2 -177.23(13) .
C5 C4 C3 C2 0.9(2) .
C2 C1 C6 C5 0.4(2) .
C2 C1 C6 C7 -179.27(14) .
C4 C9 C4 C5 -111.35(14) 2
C4 C9 C4 C3 66.67(12) 2
C4 C5 C6 C1 -0.4(2) .
C4 C5 C6 C7 179.27(14) .
C3 C2 C1 C6 0.2(2) .
C3 C2 C1 N1 -178.31(14) .
C1 C2 C3 C4 -0.9(2) .
C6 C5 C4 C9 177.84(14) .
C6 C5 C4 C3 -0.3(2) .
N1 C1 C6 C5 178.93(15) .
N1 C1 C6 C7 -0.7(2) .
C8 C2 C3 C4 177.42(14) .
C8 C2 C1 C6 -178.10(14) .
C8 C2 C1 N1 3.4(2) .
