#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/40/7204012.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_7204012
loop_
_publ_author_name
'Antipin, Mikhail Yu.'
'Timofeeva, Tatiana V.'
'Clark, Ronald D.'
'Nesterov, Vladimir N.'
'Dolgushin, Fedor M.'
'Wu, Javier'
'Leyderman, Alex'
_publ_section_title
;
 Crystal structures and molecular mechanics calculation of nonlinear
 optical compounds: 2-cyclooctylamino-5-nitropyridine (COANP) and
 2-adamantylamino-5-nitropyridine (AANP). New polymorphic modification
 of AANP and electro-optical effects
;
_journal_issue                   2
_journal_name_full               'Journal of Materials Chemistry'
_journal_page_first              351
_journal_paper_doi               10.1039/b005822j
_journal_volume                  11
_journal_year                    2001
_chemical_formula_sum            'C15 H19 N3 O2'
_chemical_formula_weight         273.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.991(2)
_cell_length_b                   26.326(5)
_cell_length_c                   6.5880(13)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     1385.9(5)
_computing_structure_refinement  'SHELXTL PLUS 5'
_computing_structure_solution    'SHELXTL PLUS 5'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'Enraf Nonius CAD4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1229
_diffrn_reflns_av_sigmaI/netI    0.3648
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2051
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.66
_diffrn_standards_decay_%        4
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow '
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4.63(539)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.863
_refine_ls_goodness_of_fit_obs   1.360
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1285
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.796
_refine_ls_restrained_S_obs      1.355
_refine_ls_R_factor_all          0.3264
_refine_ls_R_factor_obs          0.0659
_refine_ls_shift/esd_max         0.042
_refine_ls_shift/esd_mean        0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0143P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2310
_refine_ls_wR_factor_obs         0.0701
_reflns_number_observed          329
_reflns_number_total             1322
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b005822j.txt
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0143P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0143P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               7204012
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O -0.4215(14) 0.7376(4) -0.0728(16) 0.091(5) Uani 1 d . .
O2 O -0.3768(15) 0.8118(5) -0.2028(14) 0.101(5) Uani 1 d . .
N1 N -0.0959(14) 0.8592(4) 0.2755(20) 0.065(4) Uani 1 d . .
N2 N 0.0382(13) 0.8365(4) 0.5712(16) 0.049(3) Uani 1 d . .
H2N H 0.0503(13) 0.8142(4) 0.6656(16) 0.059 Uiso 1 calc R .
N3 N -0.3548(15) 0.7785(7) -0.0813(23) 0.068(5) Uani 1 d . .
C1 C -0.0650(18) 0.8231(5) 0.4283(23) 0.047(4) Uani 1 d . .
C2 C -0.1272(17) 0.7734(5) 0.4129(25) 0.059(4) Uani 1 d . .
H2A H -0.0947(17) 0.7490(5) 0.5072(25) 0.071 Uiso 1 calc R .
C3 C -0.2325(17) 0.7609(6) 0.2643(24) 0.071(5) Uani 1 d . .
H3A H -0.2864(17) 0.7295(6) 0.2623(24) 0.085 Uiso 1 calc R .
C4 C -0.2590(22) 0.7974(6) 0.1093(25) 0.051(4) Uani 1 d . .
C5 C -0.1952(17) 0.8441(6) 0.1183(28) 0.073(6) Uani 1 d . .
H5A H -0.2191(17) 0.8671(6) 0.0148(28) 0.088 Uiso 1 calc R .
C6 C 0.1369(17) 0.8823(6) 0.6000(20) 0.041(4) Uani 1 d . .
C7 C 0.2580(16) 0.8905(5) 0.4264(21) 0.060(4) Uani 1 d . .
H7A H 0.1954(16) 0.8946(5) 0.3014(21) 0.072 Uiso 1 calc R .
H7B H 0.3282(16) 0.8607(5) 0.4122(21) 0.072 Uiso 1 calc R .
C8 C 0.3693(17) 0.9371(6) 0.4585(25) 0.054(4) Uani 1 d . .
H8A H 0.4440(17) 0.9420(6) 0.3422(25) 0.065 Uiso 1 calc R .
C9 C 0.2606(19) 0.9824(6) 0.4872(17) 0.066(5) Uani 1 d . .
H9A H 0.1969(19) 0.9884(6) 0.3642(17) 0.080 Uiso 1 calc R .
H9B H 0.3300(19) 1.0120(6) 0.5119(17) 0.080 Uiso 1 calc R .
C10 C 0.1412(19) 0.9753(6) 0.6636(23) 0.061(4) Uani 1 d . .
H10A H 0.0706(19) 1.0055(6) 0.6798(23) 0.073 Uiso 1 calc R .
C11 C 0.2488(17) 0.9667(6) 0.8574(18) 0.063(5) Uani 1 d . .
H11A H 0.3209(17) 0.9958(6) 0.8803(18) 0.075 Uiso 1 calc R .
H11B H 0.1765(17) 0.9628(6) 0.9747(18) 0.075 Uiso 1 calc R .
C12 C 0.3508(17) 0.9207(6) 0.8298(18) 0.052(4) Uani 1 d . .
H12A H 0.4147(17) 0.9150(6) 0.9547(18) 0.063 Uiso 1 calc R .
C13 C 0.2434(18) 0.8742(5) 0.7913(17) 0.055(4) Uani 1 d . .
H13A H 0.1710(18) 0.8683(5) 0.9070(17) 0.066 Uiso 1 calc R .
H13B H 0.3143(18) 0.8447(5) 0.7737(17) 0.066 Uiso 1 calc R .
C14 C 0.4733(14) 0.9281(6) 0.6579(23) 0.062(4) Uani 1 d . .
H14A H 0.5433(14) 0.8982(6) 0.6432(23) 0.075 Uiso 1 calc R .
H14B H 0.5447(14) 0.9571(6) 0.6849(23) 0.075 Uiso 1 calc R .
C15 C 0.0316(14) 0.9278(5) 0.6328(25) 0.059(4) Uani 1 d . .
H15A H -0.0384(14) 0.9227(5) 0.7513(25) 0.071 Uiso 1 calc R .
H15B H -0.0410(14) 0.9327(5) 0.5164(25) 0.071 Uiso 1 calc R .
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C5 N1 C1 116.7(12) . . ?
C1 N2 C6 131.5(12) . . ?
O1 N3 O2 128.3(17) . . ?
O1 N3 C4 117.9(16) . . ?
O2 N3 C4 112.2(14) . . ?
N2 C1 C2 122.0(16) . . ?
N2 C1 N1 116.5(11) . . ?
C2 C1 N1 121.1(16) . . ?
C3 C2 C1 120.5(16) . . ?
C2 C3 C4 117.1(14) . . ?
C5 C4 C3 122.5(16) . . ?
C5 C4 N3 121.4(16) . . ?
C3 C4 N3 116.0(13) . . ?
C4 C5 N1 121.6(16) . . ?
N2 C6 C15 112.5(12) . . ?
N2 C6 C7 111.5(11) . . ?
C15 C6 C7 111.0(13) . . ?
N2 C6 C13 107.0(12) . . ?
C15 C6 C13 107.9(12) . . ?
C7 C6 C13 106.6(11) . . ?
C6 C7 C8 112.4(13) . . ?
C9 C8 C7 108.7(13) . . ?
C9 C8 C14 108.9(13) . . ?
C7 C8 C14 107.5(13) . . ?
C8 C9 C10 111.5(13) . . ?
C9 C10 C15 110.9(14) . . ?
C9 C10 C11 107.4(12) . . ?
C15 C10 C11 107.6(13) . . ?
C12 C11 C10 109.0(11) . . ?
C11 C12 C14 110.3(12) . . ?
C11 C12 C13 111.8(12) . . ?
C14 C12 C13 110.2(12) . . ?
C12 C13 C6 109.9(12) . . ?
C12 C14 C8 107.7(9) . . ?
C6 C15 C10 110.7(11) . . ?
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
O1 N3 1.20(2) . ?
O2 N3 1.20(2) . ?
N1 C5 1.36(2) . ?
N1 C1 1.41(2) . ?
N2 C1 1.30(2) . ?
N2 C6 1.454(15) . ?
N3 C4 1.55(2) . ?
C1 C2 1.40(2) . ?
C2 C3 1.33(2) . ?
C3 C4 1.42(2) . ?
C4 C5 1.33(2) . ?
C6 C15 1.478(15) . ?
C6 C7 1.51(2) . ?
C6 C13 1.54(2) . ?
C7 C8 1.53(2) . ?
C8 C9 1.49(2) . ?
C8 C14 1.57(2) . ?
C9 C10 1.51(2) . ?
C10 C15 1.54(2) . ?
C10 C11 1.56(2) . ?
C11 C12 1.47(2) . ?
C12 C14 1.51(2) . ?
C12 C13 1.52(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3073079
