#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/86/4508682.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4508682
loop_
_publ_author_name
'Yuge, Tetsuharu'
'Miyata, Mikiji'
'Tohnai, Norimitsu'
_publ_section_title
;
 Novel Design of Tunable Organic Clay Mimic Structures Based on the
 Connection of One-Dimensional Supramolecular Synthons
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1271
_journal_paper_doi               10.1021/cg0600851
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C12 H18 N O2'
_chemical_formula_weight         208.28
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 89.73(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.146(4)
_cell_length_b                   6.448(1)
_cell_length_c                   22.899(5)
_cell_measurement_reflns_used    8933
_cell_measurement_temperature    297.2
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.9
_cell_volume                     2531.6(9)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 0.9443
_diffrn_measured_fraction_theta_max 0.9443
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5419
_diffrn_reflns_av_R_equivalents  0.112
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11776
_diffrn_reflns_theta_full        68.21
_diffrn_reflns_theta_max         68.21
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.700
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.619
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2188
_refine_ls_R_factor_gt           0.1182
_refine_ls_shift/su_max          0.0004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.05000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.3328
_reflns_number_gt                1039
_reflns_number_total             2188
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            cg0600851sup2.cif
_cod_data_source_block           BPDCA_tAm_
_cod_original_cell_volume        2531.4(9)
_cod_original_formula_sum        'C12 H18 N O2 '
_cod_database_code               4508682
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+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_calc_flag
O(1) O 0.8306(2) 0.5389(5) 0.1544(2) 0.111(1) Uani 1.00 d
O(2) O 0.7965(2) 0.2337(4) 0.1912(1) 0.0844(9) Uani 1.00 d
N(1) N 1.2267(2) 0.3374(5) 0.1924(1) 0.076(1) Uani 1.00 d
C(1) C 0.8326(3) 0.3461(7) 0.1543(2) 0.076(1) Uani 1.00 d
C(2) C 0.8794(2) 0.2403(6) 0.1077(2) 0.068(1) Uani 1.00 d
C(3) C 0.9004(3) 0.3438(8) 0.0582(2) 0.094(2) Uani 1.00 d
C(4) C 0.9476(3) 0.2501(8) 0.0160(2) 0.097(2) Uani 1.00 d
C(5) C 0.9745(2) 0.0494(7) 0.0228(2) 0.0635(9) Uani 1.00 d
C(6) C 0.9531(3) -0.0547(7) 0.0730(2) 0.083(1) Uani 1.00 d
C(7) C 0.9051(3) 0.0386(7) 0.1143(2) 0.081(1) Uani 1.00 d
C(8) C 1.1498(3) 0.334(1) 0.1600(3) 0.130(2) Uani 1.00 d
C(9) C 1.0964(5) 0.501(1) 0.1874(4) 0.184(4) Uani 1.00 d
C(10) C 1.1162(5) 0.112(1) 0.1734(5) 0.202(4) Uani 1.00 d
C(11) C 1.1593(9) 0.390(2) 0.0994(5) 0.258(6) Uani 1.00 d
C(12) C 1.209(1) 0.273(4) 0.0663(7) 0.39(1) Uani 1.00 d
H(1) H 0.8826 0.4817 0.0522 0.1128 Uiso 1.00 calc
H(2) H 0.9614 0.3259 -0.0180 0.1164 Uiso 1.00 calc
H(3) H 0.9714 -0.1917 0.0795 0.0996 Uiso 1.00 calc
H(4) H 0.8896 -0.0380 0.1478 0.0975 Uiso 1.00 calc
H(5) H 1.2171 0.3247 0.2332 0.0917 Uiso 1.00 calc
H(6) H 1.2583 0.2251 0.1796 0.0917 Uiso 1.00 calc
H(7) H 1.2527 0.4646 0.1848 0.0917 Uiso 1.00 calc
H(8) H 1.0867 0.4688 0.2271 0.2208 Uiso 1.00 calc
H(9) H 1.1213 0.6326 0.1846 0.2208 Uiso 1.00 calc
H(10) H 1.0484 0.5054 0.1667 0.2208 Uiso 1.00 calc
H(11) H 1.0689 0.0932 0.1525 0.2396 Uiso 1.00 calc
H(12) H 1.1063 0.0993 0.2140 0.2396 Uiso 1.00 calc
H(13) H 1.1528 0.0099 0.1615 0.2396 Uiso 1.00 calc
H(14) H 1.1787 0.5292 0.0984 0.3124 Uiso 1.00 calc
H(15) H 1.1094 0.3866 0.0818 0.3124 Uiso 1.00 calc
H(16) H 1.1889 0.1328 0.0650 0.4722 Uiso 1.00 calc
H(17) H 1.2589 0.2689 0.0842 0.4722 Uiso 1.00 calc
H(18) H 1.2126 0.3254 0.0284 0.4722 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(1) C(1) O(2) 123.7(5) 1_555 1_555 yes
O(1) C(1) C(2) 118.2(5) 1_555 1_555 yes
O(2) C(1) C(2) 118.1(5) 1_555 1_555 yes
C(1) C(2) C(3) 120.6(5) 1_555 1_555 yes
C(1) C(2) C(7) 121.4(5) 1_555 1_555 yes
C(3) C(2) C(7) 118.0(5) 1_555 1_555 yes
C(2) C(3) C(4) 121.0(6) 1_555 1_555 yes
C(3) C(4) C(5) 121.3(5) 1_555 1_555 yes
C(4) C(5) C(5) 120.8(6) 1_555 3_755 yes
C(4) C(5) C(6) 117.5(5) 1_555 1_555 yes
C(5) C(5) C(6) 121.7(6) 1_555 1_555 yes
C(5) C(6) C(7) 120.8(5) 1_555 1_555 yes
C(2) C(7) C(6) 121.4(5) 1_555 1_555 yes
N(1) C(8) C(9) 107.8(7) 1_555 1_555 yes
N(1) C(8) C(10) 103.8(6) 1_555 1_555 yes
N(1) C(8) C(11) 111.9(9) 1_555 1_555 yes
C(9) C(8) C(10) 109.9(8) 1_555 1_555 yes
C(9) C(8) C(11) 106(1) 1_555 1_555 yes
C(10) C(8) C(11) 117(1) 1_555 1_555 yes
C(8) C(11) C(12) 117(1) 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.243(7) . yes
O(2) C(1) 1.272(6) . yes
N(1) C(8) 1.516(8) . yes
C(1) C(2) 1.497(7) . yes
C(2) C(3) 1.361(7) . yes
C(2) C(7) 1.382(8) . yes
C(3) C(4) 1.395(7) . yes
C(4) C(5) 1.383(8) . yes
C(5) C(5) 1.502(9) 3_755 yes
C(5) C(6) 1.379(7) . yes
C(6) C(7) 1.388(7) . yes
C(8) C(9) 1.548(7) . yes
C(8) C(10) 1.57(1) . yes
C(8) C(11) 1.44(2) . yes
C(11) C(12) 1.371(8) . yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
O(1) N(1) 2.761(6) 5_455
O(1) C(12) 3.27(2) 5_455
O(1) C(7) 3.584(8) 1_565
O(2) N(1) 2.775(5) 2_755
O(2) N(1) 2.822(6) 5_445
O(2) C(10) 3.54(1) 2_755
O(2) C(8) 3.592(10) 2_755
C(12) C(12) 3.35(4) 7_755
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O(1) C(1) C(2) C(3) -18.2(9) 1_555 1_555 1_555 1_555 yes
O(1) C(1) C(2) C(7) 159.2(6) 1_555 1_555 1_555 1_555 yes
O(2) C(1) C(2) C(3) 161.0(6) 1_555 1_555 1_555 1_555 yes
O(2) C(1) C(2) C(7) -21.5(8) 1_555 1_555 1_555 1_555 yes
N(1) C(8) C(11) C(12) 58(2) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(4) 176.4(6) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(7) C(6) -175.3(5) 1_555 1_555 1_555 1_555 yes
C(2) C(3) C(4) C(5) 0(1) 1_555 1_555 1_555 1_555 yes
C(2) C(7) C(6) C(5) -2.4(9) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(7) C(6) 2.2(9) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(5) C(5) -179.7(6) 1_555 1_555 1_555 3_755 yes
C(3) C(4) C(5) C(6) -0.3(10) 1_555 1_555 1_555 1_555 yes
C(4) C(3) C(2) C(7) -1.1(10) 1_555 1_555 1_555 1_555 yes
C(4) C(5) C(5) C(4) -180.0 1_555 1_555 3_755 3_755 yes
C(4) C(5) C(5) C(6) 0(1) 1_555 1_555 3_755 3_755 yes
C(4) C(5) C(6) C(7) 1.3(8) 1_555 1_555 1_555 1_555 yes
C(5) C(5) C(6) C(7) 179.2(6) 1_555 3_755 3_755 3_755 yes
C(6) C(5) C(5) C(6) 180.0 1_555 1_555 3_755 3_755 yes
C(9) C(8) C(11) C(12) 175(2) 1_555 1_555 1_555 1_555 yes
C(10) C(8) C(11) C(12) -61(2) 1_555 1_555 1_555 1_555 yes
