#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/22/4112222.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_4112222
loop_
_publ_author_name
'Kazuki Sada'
'Katsunari Inoue'
'Tomoyuki Tanaka'
'Akira Tanaka'
'Attila Epergyes'
'Sadamu Nagahama'
'Akikazu Matsumoto'
'Mikiji Miyata'
_publ_section_title
;
 Organic Layered Crystals with Adjustable Interlayer Distances of
 1-Naphthylmethylammoniumn-Alkanoates and Isomerism of Hydrogen-Bond
 Networks by Steric Dimension
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1764
_journal_page_last               1771
_journal_paper_doi               10.1021/ja038379n
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.38
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8255(5)
_cell_length_b                   24.000(1)
_cell_length_c                   5.9437(2)
_cell_measurement_reflns_used    9459
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      50.4
_cell_measurement_theta_min      5.2
_cell_volume                     1686.89(12)
_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    SIR88
_diffrn_measured_fraction_theta_full 0.9795
_diffrn_measured_fraction_theta_max 0.9795
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17195
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.751
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Higashi, 1999)'
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       unknown
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_Flack   0.9(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     209
_refine_ls_number_reflns         1771
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.0055
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.08000(Max(Fo²,0) + 2Fc²)/3)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1597
_reflns_number_gt                1319
_reflns_number_total             1771
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja038379nsi20030907_090921.cif
_cod_data_source_block           sada
_cod_original_cell_volume        1686.9(1)
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C20 H19 N O2 '
_cod_database_code               4112222
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-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 0.1365(3) 0.0925(1) 0.9974(4) 0.0865(9) Uani 1.00 d
O(2) O 0.2200(2) 0.0677(1) 0.6826(4) 0.0685(7) Uani 1.00 d
N(1) N 0.1302(2) 0.0132(1) 0.3138(5) 0.0596(7) Uani 1.00 d
C(1) C 0.0413(8) 0.2739(2) 0.074(1) 0.138(2) Uani 1.00 d
C(2) C 0.0936(5) 0.2315(2) 0.1907(10) 0.104(2) Uani 1.00 d
C(3) C 0.0455(4) 0.2110(2) 0.3840(8) 0.085(1) Uani 1.00 d
C(4) C -0.0546(5) 0.2339(2) 0.460(1) 0.097(2) Uani 1.00 d
C(5) C -0.1058(5) 0.2762(2) 0.330(1) 0.122(2) Uani 1.00 d
C(6) C 0.1076(4) 0.1638(2) 0.4929(8) 0.077(1) Uani 1.00 d
C(7) C 0.0914(3) 0.1437(2) 0.6838(8) 0.076(1) Uani 1.00 d
C(8) C 0.1547(3) 0.0981(1) 0.7924(6) 0.0548(7) Uani 1.00 d
C(9) C -0.0140(3) -0.0424(1) 0.5240(6) 0.0553(8) Uani 1.00 d
C(10) C 0.0666(3) -0.0591(1) 0.6742(7) 0.0637(9) Uani 1.00 d
C(11) C 0.0418(3) -0.0962(2) 0.8528(7) 0.074(1) Uani 1.00 d
C(12) C -0.0643(3) -0.1156(2) 0.8782(7) 0.071(1) Uani 1.00 d
C(13) C -0.1514(3) -0.1004(1) 0.7277(7) 0.0623(9) Uani 1.00 d
C(14) C -0.2628(3) -0.1219(2) 0.7479(7) 0.074(1) Uani 1.00 d
C(15) C -0.3445(3) -0.1085(2) 0.6001(9) 0.080(1) Uani 1.00 d
C(16) C -0.3212(3) -0.0716(2) 0.4231(9) 0.081(1) Uani 1.00 d
C(17) C -0.2154(3) -0.0495(2) 0.3994(7) 0.069(1) Uani 1.00 d
C(18) C -0.1271(3) -0.0635(1) 0.5473(6) 0.0559(8) Uani 1.00 d
C(19) C 0.0094(3) -0.0027(2) 0.3364(6) 0.0636(9) Uani 1.00 d
C(20) C -0.0560(8) 0.2962(2) 0.140(1) 0.144(3) Uani 1.00 d
H(1) H 0.0763 0.2878 -0.0581 0.1651 Uiso 1.00 calc
H(2) H 0.1629 0.2165 0.1372 0.1250 Uiso 1.00 calc
H(3) H -0.0882 0.2214 0.5961 0.1168 Uiso 1.00 calc
H(4) H -0.1765 0.2911 0.3768 0.1464 Uiso 1.00 calc
H(5) H -0.0901 0.3255 0.0566 0.1730 Uiso 1.00 calc
H(6) H 0.1661 0.1472 0.4065 0.0923 Uiso 1.00 calc
H(7) H 0.0316 0.1596 0.7689 0.0915 Uiso 1.00 calc
H(8) H 0.1415 -0.0453 0.6583 0.0764 Uiso 1.00 calc
H(9) H 0.0997 -0.1072 0.9542 0.0890 Uiso 1.00 calc
H(10) H -0.0808 -0.1401 0.9995 0.0852 Uiso 1.00 calc
H(11) H -0.2800 -0.1463 0.8687 0.0893 Uiso 1.00 calc
H(12) H -0.4180 -0.1239 0.6157 0.0965 Uiso 1.00 calc
H(13) H -0.3791 -0.0620 0.3192 0.0974 Uiso 1.00 calc
H(14) H -0.2012 -0.0241 0.2802 0.0823 Uiso 1.00 calc
H(15) H -0.0335 0.0302 0.3617 0.0763 Uiso 1.00 calc
H(16) H -0.0142 -0.0196 0.1996 0.0763 Uiso 1.00 calc
H(17) H 0.1396 0.0366 0.2055 0.1098 Uiso 1.00 calc
H(18) H 0.1733 -0.0109 0.2835 0.1098 Uiso 1.00 calc
H(19) H 0.1621 0.0355 0.4380 0.1098 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
C(2) C(1) C(20) 122.7(8) 1_555 1_555 yes
C(1) C(2) C(3) 119.9(7) 1_555 1_555 yes
C(2) C(3) C(4) 119.1(5) 1_555 1_555 yes
C(2) C(3) C(6) 115.5(5) 1_555 1_555 yes
C(4) C(3) C(6) 125.4(5) 1_555 1_555 yes
C(3) C(4) C(5) 118.4(6) 1_555 1_555 yes
C(4) C(5) C(20) 121.4(7) 1_555 1_555 yes
C(3) C(6) C(7) 127.6(5) 1_555 1_555 yes
C(6) C(7) C(8) 127.4(5) 1_555 1_555 yes
O(1) C(8) O(2) 123.8(4) 1_555 1_555 yes
O(1) C(8) C(7) 114.9(4) 1_555 1_555 yes
O(2) C(8) C(7) 121.3(3) 1_555 1_555 yes
C(10) C(9) C(18) 118.9(3) 1_555 1_555 yes
C(10) C(9) C(19) 123.1(3) 1_555 1_555 yes
C(18) C(9) C(19) 117.9(3) 1_555 1_555 yes
C(9) C(10) C(11) 122.0(3) 1_555 1_555 yes
C(10) C(11) C(12) 119.7(4) 1_555 1_555 yes
C(11) C(12) C(13) 121.2(4) 1_555 1_555 yes
C(12) C(13) C(14) 122.0(4) 1_555 1_555 yes
C(12) C(13) C(18) 119.5(3) 1_555 1_555 yes
C(14) C(13) C(18) 118.5(4) 1_555 1_555 yes
C(13) C(14) C(15) 121.7(4) 1_555 1_555 yes
C(14) C(15) C(16) 120.0(3) 1_555 1_555 yes
C(15) C(16) C(17) 120.2(4) 1_555 1_555 yes
C(16) C(17) C(18) 121.6(4) 1_555 1_555 yes
C(9) C(18) C(13) 118.7(3) 1_555 1_555 yes
C(9) C(18) C(17) 123.2(4) 1_555 1_555 yes
C(13) C(18) C(17) 118.1(3) 1_555 1_555 yes
N(1) C(19) C(9) 114.2(3) 1_555 1_555 yes
C(1) C(20) C(5) 118.5(6) 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(8) 1.245(5) yes
O(2) C(8) 1.247(4) yes
N(1) C(19) 1.485(4) yes
C(1) C(2) 1.377(8) yes
C(1) C(20) 1.33(1) yes
C(2) C(3) 1.374(8) yes
C(3) C(4) 1.381(8) yes
C(3) C(6) 1.497(6) yes
C(4) C(5) 1.412(8) yes
C(5) C(20) 1.36(1) yes
C(6) C(7) 1.247(6) yes
C(7) C(8) 1.475(6) yes
C(9) C(10) 1.365(5) yes
C(9) C(18) 1.437(5) yes
C(9) C(19) 1.492(5) yes
C(10) C(11) 1.416(6) yes
C(11) C(12) 1.347(6) yes
C(12) C(13) 1.413(6) yes
C(13) C(14) 1.420(5) yes
C(13) C(18) 1.421(5) yes
C(14) C(15) 1.345(6) yes
C(15) C(16) 1.401(7) yes
C(16) C(17) 1.366(6) yes
C(17) C(18) 1.405(5) 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) 2.677(4) 1_556
O(1) C(19) 3.398(5) 1_556
O(1) C(6) 3.423(5) 1_556
O(1) C(15) 3.527(5) 2_455
O(1) C(2) 3.565(6) 1_556
O(2) N(1) 2.741(4) 2_555
O(2) N(1) 2.765(4) .
O(2) C(11) 3.499(5) 2_554
O(2) C(10) 3.541(4) .
N(1) C(8) 3.511(4) .
C(15) C(19) 3.591(6) 2_455
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(8) C(7) C(6) 167.3(5) 1_555 1_555 1_555 1_555 yes
O(2) C(8) C(7) C(6) -13.4(7) 1_555 1_555 1_555 1_555 yes
N(1) C(19) C(9) C(10) 5.3(5) 1_555 1_555 1_555 1_555 yes
N(1) C(19) C(9) C(18) -175.2(3) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(4) -0.7(8) 1_555 1_555 1_555 1_555 yes
C(1) C(2) C(3) C(6) 178.2(5) 1_555 1_555 1_555 1_555 yes
C(1) C(20) C(5) C(4) 1.8(10) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(20) C(5) 0(1) 1_555 1_555 1_555 1_555 yes
C(2) C(3) C(4) C(5) 2.3(7) 1_555 1_555 1_555 1_555 yes
C(2) C(3) C(6) C(7) 168.4(5) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(1) C(20) 0(1) 1_555 1_555 1_555 1_555 yes
C(3) C(4) C(5) C(20) -3.0(8) 1_555 1_555 1_555 1_555 yes
C(3) C(6) C(7) C(8) -178.4(4) 1_555 1_555 1_555 1_555 yes
C(4) C(3) C(6) C(7) -12.9(8) 1_555 1_555 1_555 1_555 yes
C(5) C(4) C(3) C(6) -176.4(4) 1_555 1_555 1_555 1_555 yes
C(9) C(10) C(11) C(12) -0.4(6) 1_555 1_555 1_555 1_555 yes
C(9) C(18) C(13) C(12) -0.3(5) 1_555 1_555 1_555 1_555 yes
C(9) C(18) C(13) C(14) -178.9(4) 1_555 1_555 1_555 1_555 yes
C(9) C(18) C(17) C(16) 178.1(4) 1_555 1_555 1_555 1_555 yes
C(10) C(9) C(18) C(13) 0.8(5) 1_555 1_555 1_555 1_555 yes
C(10) C(9) C(18) C(17) -179.0(4) 1_555 1_555 1_555 1_555 yes
C(10) C(11) C(12) C(13) 0.9(7) 1_555 1_555 1_555 1_555 yes
C(11) C(10) C(9) C(18) -0.4(6) 1_555 1_555 1_555 1_555 yes
C(11) C(10) C(9) C(19) 179.1(4) 1_555 1_555 1_555 1_555 yes
C(11) C(12) C(13) C(14) 178.0(4) 1_555 1_555 1_555 1_555 yes
C(11) C(12) C(13) C(18) -0.5(6) 1_555 1_555 1_555 1_555 yes
C(12) C(13) C(14) C(15) -178.0(4) 1_555 1_555 1_555 1_555 yes
C(12) C(13) C(18) C(17) 179.4(4) 1_555 1_555 1_555 1_555 yes
C(13) C(14) C(15) C(16) -1.2(7) 1_555 1_555 1_555 1_555 yes
C(13) C(18) C(9) C(19) -178.7(3) 1_555 1_555 1_555 1_555 yes
C(13) C(18) C(17) C(16) -1.7(6) 1_555 1_555 1_555 1_555 yes
C(14) C(13) C(18) C(17) 0.8(5) 1_555 1_555 1_555 1_555 yes
C(14) C(15) C(16) C(17) 0.3(8) 1_555 1_555 1_555 1_555 yes
C(15) C(14) C(13) C(18) 0.6(6) 1_555 1_555 1_555 1_555 yes
C(15) C(16) C(17) C(18) 1.1(7) 1_555 1_555 1_555 1_555 yes
C(17) C(18) C(9) C(19) 1.5(5) 1_555 1_555 1_555 1_555 yes
