#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:20:38 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180473 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/42/7214276.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_7214276
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                 133.440(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.9037(14)
_cell_length_b                   8.0121(8)
_cell_length_c                   14.0696(9)
_cell_measurement_reflns_used    1051
_cell_measurement_temperature    178(2)
_cell_measurement_theta_max      29.0332
_cell_measurement_theta_min      4.3161
_cell_volume                     1465.4(2)
_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      178(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.867
_diffrn_measurement_device_type  'Mo Kα'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3773
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.10
_diffrn_reflns_theta_min         4.32
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92291
_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    1.153
_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         0.188
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0755
_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
'calc w=1/[σ²(Fo²)+(0.0730P)²+0.1461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1451
_reflns_number_gt                1180
_reflns_number_total             1701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41869c3.cif
_cod_data_source_block           MBDA-Form-II-178
_cod_database_code               7214276
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 0.1458(2) 0.2500 0.0328(5) Uani 1 2 d S
H9A H -0.0284 0.2186 0.1747 0.039 Uiso 0.50 1 calc PR
H9B H 0.0284 0.2186 0.3253 0.039 Uiso 0.50 1 calc PR
C5 C 0.18360(11) 0.03593(17) 0.41020(14) 0.0311(4) Uani 1 1 d .
H5 H 0.1969 0.1019 0.4766 0.037 Uiso 1 1 calc R
C2 C 0.14431(11) -0.15875(17) 0.21702(13) 0.0314(4) Uani 1 1 d .
C4 C 0.08611(10) 0.04198(17) 0.28397(13) 0.0288(3) Uani 1 1 d .
C3 C 0.06942(10) -0.05622(17) 0.18959(13) 0.0292(3) Uani 1 1 d .
H3 H 0.0038 -0.0528 0.1025 0.035 Uiso 1 1 calc R
C1 C 0.24193(11) -0.16158(18) 0.34509(14) 0.0330(4) Uani 1 1 d .
C6 C 0.26203(10) -0.06289(18) 0.44259(14) 0.0327(4) Uani 1 1 d .
N1 N 0.32055(12) -0.2583(2) 0.37458(19) 0.0512(4) Uani 1 1 d .
C8 C 0.12099(13) -0.2702(2) 0.11324(16) 0.0464(5) Uani 1 1 d .
H8A H 0.1257 -0.3872 0.1372 0.070 Uiso 1 1 calc R
H8B H 0.1707 -0.2488 0.1058 0.070 Uiso 1 1 calc R
H8C H 0.0513 -0.2470 0.0291 0.070 Uiso 1 1 calc R
C7 C 0.36670(11) -0.0653(2) 0.57992(15) 0.0459(5) Uani 1 1 d .
H7A H 0.4185 -0.0294 0.5790 0.069 Uiso 1 1 calc R
H7B H 0.3825 -0.1787 0.6153 0.069 Uiso 1 1 calc R
H7C H 0.3672 0.0108 0.6349 0.069 Uiso 1 1 calc R
H1A H 0.3039(17) -0.341(3) 0.313(2) 0.081(7) Uiso 1 1 d .
H1B H 0.3712(19) -0.286(3) 0.457(2) 0.075(7) 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 0.0400(11) 0.0246(10) 0.0424(11) 0.000 0.0317(10) 0.000
C5 0.0357(8) 0.0291(8) 0.0333(7) -0.0061(6) 0.0256(7) -0.0098(6)
C2 0.0359(8) 0.0304(8) 0.0363(8) 0.0025(6) 0.0281(7) 0.0005(6)
C4 0.0332(7) 0.0249(7) 0.0361(7) -0.0002(6) 0.0269(7) -0.0037(6)
C3 0.0290(7) 0.0302(8) 0.0296(7) 0.0007(6) 0.0206(6) -0.0016(6)
C1 0.0323(8) 0.0318(8) 0.0411(8) 0.0065(6) 0.0277(7) 0.0022(6)
C6 0.0303(7) 0.0319(8) 0.0345(8) 0.0027(6) 0.0217(7) -0.0060(6)
N1 0.0400(8) 0.0559(10) 0.0578(10) 0.0088(8) 0.0336(8) 0.0146(7)
C8 0.0546(10) 0.0501(11) 0.0454(9) -0.0015(8) 0.0386(9) 0.0075(8)
C7 0.0338(8) 0.0482(10) 0.0391(9) 0.0042(7) 0.0187(8) -0.0088(7)
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
_geom_angle_site_symmetry_3
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 113.21(16) . 2
C4 C5 H5 118.8 . .
C6 C5 H5 118.8 . .
C6 C5 C4 122.45(13) . .
C3 C2 C1 118.72(13) . .
C3 C2 C8 120.86(13) . .
C1 C2 C8 120.38(13) . .
C5 C4 C9 122.27(11) . .
C3 C4 C9 120.51(11) . .
C3 C4 C5 117.18(12) . .
C2 C3 C4 122.72(13) . .
C2 C3 H3 118.6 . .
C4 C3 H3 118.6 . .
C6 C1 C2 120.21(13) . .
N1 C1 C2 120.08(14) . .
N1 C1 C6 119.67(15) . .
C5 C6 C1 118.71(13) . .
C5 C6 C7 120.94(14) . .
C1 C6 C7 120.35(13) . .
C1 N1 H1A 119.3(13) . .
C1 N1 H1B 116.4(15) . .
H1A N1 H1B 114(2) . .
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 0.9900 .
C9 H9B 0.9900 .
C9 C4 1.5112(17) .
C9 C4 1.5112(17) 2
C5 H5 0.9500 .
C5 C4 1.3929(19) .
C5 C6 1.388(2) .
C2 C3 1.3821(18) .
C2 C1 1.404(2) .
C2 C8 1.505(2) .
C4 C3 1.3877(19) .
C3 H3 0.9500 .
C1 C6 1.399(2) .
C1 N1 1.3968(19) .
C6 C7 1.505(2) .
N1 H1A 0.96(2) .
N1 H1B 0.88(2) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
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 -177.17(12) .
C5 C4 C3 C2 0.9(2) .
C2 C1 C6 C5 0.5(2) .
C2 C1 C6 C7 -179.84(13) .
C4 C9 C4 C5 -111.54(13) 2
C4 C9 C4 C3 66.45(11) 2
C4 C5 C6 C1 -0.8(2) .
C4 C5 C6 C7 179.57(13) .
C3 C2 C1 C6 0.4(2) .
C3 C2 C1 N1 -177.20(13) .
C1 C2 C3 C4 -1.2(2) .
C6 C5 C4 C9 178.14(12) .
C6 C5 C4 C3 0.1(2) .
N1 C1 C6 C5 178.16(13) .
N1 C1 C6 C7 -2.2(2) .
C8 C2 C3 C4 176.60(13) .
C8 C2 C1 C6 -177.36(13) .
C8 C2 C1 N1 5.0(2) .
