#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/40/7204014.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_7204014
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            'C13 H19 N3 O2'
_chemical_formula_weight         249.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c 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                   26.099(5)
_cell_length_b                   6.637(2)
_cell_length_c                   7.555(2)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    167(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      11
_cell_volume                     1308.7(6)
_computing_structure_refinement  'SHELXTL PLUS 5'
_computing_structure_solution    'SHELXTL PLUS 5'
_diffrn_ambient_temperature      167(2)
_diffrn_measurement_device       'Siemens PC/P3'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0861
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1622
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.56
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.99(283)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.021
_refine_ls_goodness_of_fit_obs   1.205
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1570
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.322
_refine_ls_restrained_S_obs      1.204
_refine_ls_R_factor_all          0.1519
_refine_ls_R_factor_obs          0.0592
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0642P)²+0.0840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1637
_refine_ls_wR_factor_obs         0.1082
_reflns_number_observed          909
_reflns_number_total             1622
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b005822j.txt
_cod_data_source_block           conp-lt
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0642P)^2^+0.0840P] 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^)+(0.0642P)^2^+0.0840P] 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      Pca2(1)
_cod_database_code               7204014
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 0.21452(11) 0.3980(4) 0.3630(4) 0.0514(8) Uani 1 d . .
O2 O 0.29037(12) 0.2811(5) 0.3174(5) 0.0646(10) Uani 1 d . .
N1 N 0.35612(10) 0.7405(5) 0.5898(4) 0.0336(7) Uani 1 d . .
N2 N 0.34621(10) 1.0442(4) 0.7356(4) 0.0321(8) Uani 1 d . .
H2A H 0.32667(10) 1.1489(4) 0.7589(4) 0.039 Uiso 1 calc R .
N3 N 0.26187(13) 0.4114(5) 0.3754(4) 0.0381(8) Uani 1 d . .
C1 C 0.32538(13) 0.8939(5) 0.6425(4) 0.0282(8) Uani 1 d . .
C2 C 0.27190(12) 0.8945(5) 0.6073(5) 0.0308(8) Uani 1 d . .
H2B H 0.25123(12) 1.0037(5) 0.6462(5) 0.037 Uiso 1 calc R .
C3 C 0.2506(2) 0.7391(5) 0.5184(5) 0.0321(8) Uani 1 d . .
H3A H 0.2150(2) 0.7368(5) 0.4929(5) 0.038 Uiso 1 calc R .
C4 C 0.28262(14) 0.5819(5) 0.4653(5) 0.0303(8) Uani 1 d . .
C5 C 0.33446(14) 0.5917(5) 0.5008(5) 0.0319(9) Uani 1 d . .
H5A H 0.35572(14) 0.4858(5) 0.4589(5) 0.038 Uiso 1 calc R .
C6 C 0.39916(14) 1.0488(5) 0.8022(5) 0.0309(9) Uani 1 d . .
H6A H 0.42225(14) 0.9984(5) 0.7062(5) 0.037 Uiso 1 calc R .
C7 C 0.41202(14) 1.2693(6) 0.8362(6) 0.0439(10) Uani 1 d . .
H7A H 0.40564(14) 1.3450(6) 0.7255(6) 0.053 Uiso 1 calc R .
H7B H 0.38776(14) 1.3210(6) 0.9261(6) 0.053 Uiso 1 calc R .
C8 C 0.4660(2) 1.3182(7) 0.8982(6) 0.0499(11) Uani 1 d . .
H8A H 0.4702(2) 1.4663(7) 0.8938(6) 0.060 Uiso 1 calc R .
H8B H 0.4903(2) 1.2599(7) 0.8113(6) 0.060 Uiso 1 calc R .
C9 C 0.48228(14) 1.2475(8) 1.0818(6) 0.0574(13) Uani 1 d . .
H9A H 0.49297(14) 1.1047(8) 1.0730(6) 0.069 Uiso 1 calc R .
H9B H 0.51273(14) 1.3263(8) 1.1180(6) 0.069 Uiso 1 calc R .
C10 C 0.4426(2) 1.2642(8) 1.2264(7) 0.0615(14) Uani 1 d . .
H10A H 0.4599(2) 1.3116(8) 1.3352(7) 0.074 Uiso 1 calc R .
H10B H 0.4177(2) 1.3695(8) 1.1915(7) 0.074 Uiso 1 calc R .
C11 C 0.4132(2) 1.0764(7) 1.2713(6) 0.0568(12) Uani 1 d . .
H11A H 0.3919(2) 1.1062(7) 1.3767(6) 0.068 Uiso 1 calc R .
H11B H 0.4383(2) 0.9722(7) 1.3067(6) 0.068 Uiso 1 calc R .
C12 C 0.37795(15) 0.9832(7) 1.1306(6) 0.0443(10) Uani 1 d . .
H12A H 0.35194(15) 1.0849(7) 1.0971(6) 0.053 Uiso 1 calc R .
H12B H 0.35956(15) 0.8684(7) 1.1850(6) 0.053 Uiso 1 calc R .
C13 C 0.40425(14) 0.9080(6) 0.9605(5) 0.0379(10) Uani 1 d . .
H13A H 0.44111(14) 0.8874(6) 0.9855(5) 0.045 Uiso 1 calc R .
H13B H 0.38950(14) 0.7755(6) 0.9284(5) 0.045 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 117.2(3) . . ?
C1 N2 C6 125.3(3) . . ?
O2 N3 O1 121.9(3) . . ?
O2 N3 C4 120.1(3) . . ?
O1 N3 C4 118.0(3) . . ?
N2 C1 N1 118.3(3) . . ?
N2 C1 C2 119.7(3) . . ?
N1 C1 C2 121.9(3) . . ?
C3 C2 C1 119.7(3) . . ?
C2 C3 C4 117.8(4) . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 N3 120.1(3) . . ?
C3 C4 N3 120.2(3) . . ?
N1 C5 C4 123.6(3) . . ?
N2 C6 C7 106.5(3) . . ?
N2 C6 C13 109.7(3) . . ?
C7 C6 C13 115.9(3) . . ?
C8 C7 C6 117.5(3) . . ?
C7 C8 C9 118.2(4) . . ?
C10 C9 C8 116.4(4) . . ?
C11 C10 C9 117.0(4) . . ?
C10 C11 C12 118.9(4) . . ?
C11 C12 C13 116.2(3) . . ?
C6 C13 C12 114.7(3) . . ?
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 1.242(4) . ?
O2 N3 1.222(4) . ?
N1 C5 1.322(4) . ?
N1 C1 1.356(4) . ?
N2 C1 1.336(4) . ?
N2 C6 1.471(4) . ?
N3 C4 1.427(5) . ?
C1 C2 1.421(5) . ?
C2 C3 1.351(5) . ?
C3 C4 1.396(5) . ?
C4 C5 1.381(5) . ?
C6 C7 1.523(5) . ?
C6 C13 1.524(5) . ?
C7 C8 1.520(5) . ?
C8 C9 1.525(6) . ?
C9 C10 1.510(6) . ?
C10 C11 1.503(6) . ?
C11 C12 1.535(6) . ?
C12 C13 1.540(6) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 518494
