#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/66/4116621.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_4116621
loop_
_publ_author_name
'Akikazu Matsumoto'
'Toru Odani'
'Masaaki Chikada'
'Kazuki Sada'
'Mikiji Miyata'
_publ_section_title
;
 Crystal-Lattice Controlled Photopolymerization of Di(benzylammonium)
 (Z,Z)-Muconates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11122
_journal_page_last               11129
_journal_paper_doi               10.1021/ja992558g
_journal_volume                  121
_journal_year                    1999
_chemical_formula_sum            'C11 H14 N O3'
_chemical_formula_weight         208.24
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Fri Jul  2 15:46:35 1999'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                98.043(7)
_cell_angle_beta                 98.117(6)
_cell_angle_gamma                97.42(2)
_cell_formula_units_Z            2
_cell_length_a                   9.366(3)
_cell_length_b                   10.858(4)
_cell_length_c                   5.599(3)
_cell_measurement_reflns_used    1552
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      27.3
_cell_measurement_theta_min      2.7
_cell_volume                     551.7(4)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      296.2
_diffrn_detector_area_resol_mean 0.010000
_diffrn_measurement_device_type  'Rigaku RAXIS-IV'
_diffrn_radiation_detector       'Imaging Plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_av_sigmaI/netI    0.065
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2152
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         0.00
_diffrn_reflns_theta_min         0.00
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.613
_exptl_absorpt_correction_T_min  0.314
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       platelet
_exptl_crystal_F_000             222.00
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.722
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1045
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1647
_refine_ls_R_factor_gt           0.1647
_refine_ls_shift/su_max          0.0890
_refine_ls_shift/su_mean         0.0250
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[σ²(Fo²) + 0.04000(Fo²)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4025
_refine_ls_wR_factor_ref         0.4025
_reflns_number_gt                1045
_reflns_number_total             2152
_reflns_threshold_expression     >2.0sigma(I)
_cod_data_source_file            ja992558g_5.cif
_cod_data_source_block           4_OMe
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C11 H14 N O3 '
_cod_database_code               4116621
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-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 0.0125(6) 0.1104(6) 0.781(1) 0.084(2) Uani 1.00 d
O(2) O 0.5649(5) 0.3699(4) 0.2318(9) 0.056(1) Uani 1.00 d
O(3) O 0.5885(7) 0.2494(5) -0.1068(10) 0.075(2) Uani 1.00 d
N(1) N 0.3457(7) 0.5286(6) 0.269(1) 0.060(2) Uani 1.00 d
C(1) C 0.1436(9) 0.3734(9) 0.347(1) 0.069(3) Uani 1.00 d
C(2) C -0.0085(8) 0.3307(8) 0.348(2) 0.066(3) Uani 1.00 d
C(3) C -0.0518(8) 0.2547(7) 0.497(2) 0.062(2) Uani 1.00 d
C(4) C 0.0462(7) 0.1900(7) 0.633(1) 0.050(2) Uani 1.00 d
C(5) C 0.1876(9) 0.2173(8) 0.621(2) 0.072(3) Uani 1.00 d
C(6) C 0.2421(8) 0.3214(7) 0.499(2) 0.064(2) Uani 1.00 d
C(7) C -0.1439(10) 0.065(1) 0.786(2) 0.096(4) Uani 1.00 d
C(8) C 0.1877(9) 0.4669(7) 0.192(2) 0.062(2) Uani 1.00 d
C(9) C 0.5642(7) 0.2650(6) 0.111(1) 0.042(2) Uani 1.00 d
C(10) C 0.5304(8) 0.1493(6) 0.227(1) 0.051(2) Uani 1.00 d
C(11) C 0.5033(7) 0.0291(6) 0.132(1) 0.047(2) Uani 1.00 d
H(1) H -0.0801 0.3579 0.2371 0.0808 Uiso 1.00 calc
H(2) H -0.1523 0.2426 0.5133 0.0752 Uiso 1.00 calc
H(3) H 0.2553 0.1697 0.6934 0.0866 Uiso 1.00 calc
H(4) H 0.3434 0.3517 0.5217 0.0760 Uiso 1.00 calc
H(5) H -0.1902 0.1308 0.8483 0.1155 Uiso 1.00 calc
H(6) H -0.1494 0.0003 0.8881 0.1155 Uiso 1.00 calc
H(7) H -0.1918 0.0281 0.6251 0.1155 Uiso 1.00 calc
H(8) H 0.1752 0.4258 0.0277 0.0745 Uiso 1.00 calc
H(9) H 0.1269 0.5303 0.2034 0.0745 Uiso 1.00 calc
H(10) H 0.3751 0.5674 0.4525 0.0714 Uiso 1.00 calc
H(11) H 0.3772 0.6050 0.2245 0.0714 Uiso 1.00 calc
H(12) H 0.4316 0.4695 0.2511 0.0714 Uiso 1.00 calc
H(13) H 0.5281 0.1669 0.3984 0.0608 Uiso 1.00 calc
H(14) H 0.5031 -0.0306 0.2707 0.0562 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 0.003 0.002
;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 0.011 0.006
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
N N 0.006 0.003
;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_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(4) O(1) C(7) 119.6(7) 1_555 1_555 1_555 yes
C(8) N(1) H(10) 115.3(6) 1_555 1_555 1_555 no
C(8) N(1) H(11) 120.3(6) 1_555 1_555 1_555 no
C(8) N(1) H(12) 118.3(6) 1_555 1_555 1_555 no
H(10) N(1) H(11) 90.5(6) 1_555 1_555 1_555 no
H(10) N(1) H(12) 99.5(5) 1_555 1_555 1_555 no
H(11) N(1) H(12) 107.8(6) 1_555 1_555 1_555 no
C(2) C(1) C(6) 115.8(8) 1_555 1_555 1_555 yes
C(2) C(1) C(8) 120.5(7) 1_555 1_555 1_555 yes
C(6) C(1) C(8) 123.8(8) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 122.1(7) 1_555 1_555 1_555 yes
C(1) C(2) H(1) 119.0(9) 1_555 1_555 1_555 no
C(3) C(2) H(1) 118.9(8) 1_555 1_555 1_555 no
C(2) C(3) C(4) 122.4(7) 1_555 1_555 1_555 yes
C(2) C(3) H(2) 118.6(8) 1_555 1_555 1_555 no
C(4) C(3) H(2) 119.0(8) 1_555 1_555 1_555 no
O(1) C(4) C(3) 126.6(7) 1_555 1_555 1_555 yes
O(1) C(4) C(5) 116.0(7) 1_555 1_555 1_555 yes
C(3) C(4) C(5) 117.2(7) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 121.2(7) 1_555 1_555 1_555 yes
C(4) C(5) H(3) 119.9(8) 1_555 1_555 1_555 no
C(6) C(5) H(3) 118.9(8) 1_555 1_555 1_555 no
C(1) C(6) C(5) 119.3(7) 1_555 1_555 1_555 yes
C(1) C(6) H(4) 120.3(8) 1_555 1_555 1_555 no
C(5) C(6) H(4) 120.3(7) 1_555 1_555 1_555 no
O(1) C(7) H(5) 110.6(10) 1_555 1_555 1_555 no
O(1) C(7) H(6) 109.0(9) 1_555 1_555 1_555 no
O(1) C(7) H(7) 109.5(8) 1_555 1_555 1_555 no
H(5) C(7) H(6) 109.5(10) 1_555 1_555 1_555 no
H(5) C(7) H(7) 110(1) 1_555 1_555 1_555 no
H(6) C(7) H(7) 108(1) 1_555 1_555 1_555 no
N(1) C(8) C(1) 112.5(7) 1_555 1_555 1_555 yes
N(1) C(8) H(8) 108.7(8) 1_555 1_555 1_555 no
N(1) C(8) H(9) 108.7(6) 1_555 1_555 1_555 no
C(1) C(8) H(8) 108.8(7) 1_555 1_555 1_555 no
C(1) C(8) H(9) 108.5(8) 1_555 1_555 1_555 no
H(8) C(8) H(9) 109.5(8) 1_555 1_555 1_555 no
O(2) C(9) O(3) 123.3(6) 1_555 1_555 1_555 yes
O(2) C(9) C(10) 118.7(6) 1_555 1_555 1_555 yes
O(3) C(9) C(10) 117.9(6) 1_555 1_555 1_555 yes
C(9) C(10) C(11) 130.9(7) 1_555 1_555 1_555 yes
C(9) C(10) H(13) 114.2(6) 1_555 1_555 1_555 no
C(11) C(10) H(13) 114.9(7) 1_555 1_555 1_555 no
C(10) C(11) C(11) 127.8(8) 1_555 1_555 2_655 yes
C(10) C(11) H(14) 112.0(6) 1_555 1_555 1_555 no
C(11) C(11) H(14) 119.4(7) 2_655 1_555 1_555 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(4) 1.317(9) 1_555 1_555 yes
O(1) C(7) 1.49(1) 1_555 1_555 yes
O(2) C(9) 1.239(7) 1_555 1_555 yes
O(3) C(9) 1.264(8) 1_555 1_555 yes
N(1) C(8) 1.52(1) 1_555 1_555 yes
C(1) C(2) 1.44(1) 1_555 1_555 yes
C(1) C(6) 1.39(1) 1_555 1_555 yes
C(1) C(8) 1.48(1) 1_555 1_555 yes
C(2) C(3) 1.32(1) 1_555 1_555 yes
C(3) C(4) 1.43(1) 1_555 1_555 yes
C(4) C(5) 1.33(1) 1_555 1_555 yes
C(5) C(6) 1.47(1) 1_555 1_555 yes
C(9) C(10) 1.512(9) 1_555 1_555 yes
C(10) C(11) 1.317(9) 1_555 1_555 yes
C(11) C(11) 1.51(1) 1_555 2_655 yes
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
O(1) C(7) 3.47(1) 1_555 2_557
O(2) N(1) 2.822(8) 1_555 2_666
O(2) N(1) 2.856(8) 1_555 1_555
O(2) N(1) 3.327(8) 1_555 2_665
O(2) C(6) 3.570(9) 1_555 1_555
O(3) N(1) 2.721(8) 1_555 2_665
O(3) C(7) 3.47(1) 1_555 1_654
N(1) C(9) 3.408(9) 1_555 2_665
C(5) C(7) 3.49(1) 1_555 2_556
C(7) C(11) 3.50(1) 1_555 2_556
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(4) C(3) C(2) -178.3(8) 1_555 1_555 1_555 1_555 yes
O(1) C(4) C(5) C(6) -168.6(7) 1_555 1_555 1_555 1_555 yes
O(2) C(9) C(10) C(11) 169.5(8) 1_555 1_555 1_555 1_555 yes
O(3) C(9) C(10) C(11) -9(1) 1_555 1_555 1_555 1_555 yes
N(1) C(8) C(1) C(2) 163.1(7) 1_555 1_555 1_555 1_555 yes
N(1) C(8) C(1) C(6) -17(1) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(4) -12(1) 1_555 1_555 1_555 1_555 yes
C(1) C(6) C(5) C(4) -14(1) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(6) C(5) 7(1) 1_555 1_555 1_555 1_555 yes
C(2) C(3) C(4) C(5) 5(1) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(1) C(6) 5(1) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(1) C(8) -175.0(8) 1_555 1_555 1_555 1_555 yes
C(3) C(4) O(1) C(7) 10(1) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(5) C(6) 7(1) 1_555 1_555 1_555 1_555 yes
C(5) C(4) O(1) C(7) -173.8(8) 1_555 1_555 1_555 1_555 yes
C(5) C(6) C(1) C(8) -171.9(8) 1_555 1_555 1_555 1_555 yes
C(9) C(10) C(11) C(11) 0(1) 1_555 1_555 1_555 2_655 yes
C(10) C(11) C(11) C(10) 180.0 1_555 1_555 2_655 2_655 yes
