#------------------------------------------------------------------------------
#$Date: 2019-11-28 21:00:43 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244607 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/92/7239224.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_7239224
loop_
_publ_author_name
'Aboulfadl, Hanane'
'Bonin, Michel'
'Burgner, Matthias'
'Brahimi, Khadidja'
'Hulliger, Jürg'
_publ_section_title
;
 Molecular recognition at growing crystal faces revealed by phase
 sensitive second harmonic microscopy
;
_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              25145
_journal_paper_doi               10.1039/c3ra43641a
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C13 H19 N3 O2'
_chemical_formula_sum            'C13 H19 N3 O2'
_chemical_formula_weight         249.31
_chemical_melting_point          ?
_chemical_name_common            coanp
_chemical_name_systematic
; 
2-(Cyclo-octylamino)-5-nitropyridine
;
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_cell_setting           orthorhombic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.010(5)
_cell_length_b                   6.6360(13)
_cell_length_c                   7.5136(15)
_cell_measurement_reflns_used    17159
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.94
_cell_measurement_theta_min      1.70
_cell_volume                     1296.9(4)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_molecular_graphics    'SXGRAPH in WinGx 1.80.04'
_computing_publication_material  'WinGx 1.80.04'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 6.6
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9096
_diffrn_reflns_theta_full        64.72
_diffrn_reflns_theta_max         64.72
_diffrn_reflns_theta_min         3.40
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  0.9641
_exptl_absorpt_correction_T_min  0.8152
_exptl_absorpt_correction_type   'numerical on indexed faces'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0568P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                1924
_reflns_number_total             2055
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra43641a.txt
_cod_data_source_block           coanp
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'unknown' was changed to
'?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7239224
_audit_contact_author            'M.Bonin* & K.Schenk**'
_exptl_absorpt_correction_details 'STOE X-RED'
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.67464(6) 0.3919(3) 0.8275(2) 0.0140(4) Uani 1 1 d .
C2 C 0.72815(6) 0.3949(3) 0.7906(2) 0.0141(4) Uani 1 1 d .
H2 H 0.7480(4) 0.502(2) 0.8258(8) 0.017 Uiso 1 1 calc R
C3 C 0.74946(7) 0.2378(2) 0.7026(2) 0.0151(4) Uani 1 1 d .
H3 H 0.7829(8) 0.2345(2) 0.6799(5) 0.018 Uiso 1 1 calc R
C4 C 0.71713(6) 0.0805(3) 0.6484(2) 0.0148(4) Uani 1 1 d .
C5 C 0.66516(6) 0.0897(3) 0.6857(2) 0.0157(4) Uani 1 1 d .
H5 H 0.6440(5) -0.017(2) 0.6458(9) 0.019 Uiso 1 1 calc R
C6 C 0.60081(6) 0.5495(2) 0.9867(2) 0.0143(4) Uani 1 1 d .
H6 H 0.5787(5) 0.5032(10) 0.8951(19) 0.017 Uiso 1 1 calc R
C7 C 0.58841(6) 0.7703(3) 1.0234(2) 0.0197(4) Uani 1 1 d .
H7A H 0.6127(4) 0.8196(8) 1.1158(14) 0.024 Uiso 1 1 calc R
H7B H 0.59551(13) 0.8479(12) 0.9127(16) 0.024 Uiso 1 1 calc R
C8 C 0.53404(6) 0.8217(3) 1.0843(2) 0.0229(4) Uani 1 1 d .
H8A H 0.5101(4) 0.7683(8) 0.9958(14) 0.027 Uiso 1 1 calc R
H8B H 0.53054(9) 0.968(2) 1.0830(2) 0.027 Uiso 1 1 calc R
C9 C 0.51677(6) 0.7463(3) 1.2678(3) 0.0251(4) Uani 1 1 d .
H9A H 0.50680(16) 0.604(2) 1.2572(3) 0.030 Uiso 1 1 calc R
H9B H 0.4862(4) 0.8221(10) 1.3038(6) 0.030 Uiso 1 1 calc R
C10 C 0.55749(7) 0.7649(3) 1.4161(3) 0.0273(5) Uani 1 1 d .
H10A H 0.5822(4) 0.8682(17) 1.3811(6) 0.033 Uiso 1 1 calc R
H10B H 0.5404(3) 0.8117(8) 1.5240(17) 0.033 Uiso 1 1 calc R
C11 C 0.58702(7) 0.5734(3) 1.4603(2) 0.0266(5) Uani 1 1 d .
H11A H 0.5612(4) 0.4679(18) 1.4966(6) 0.032 Uiso 1 1 calc R
H11B H 0.6090(4) 0.6023(5) 1.5679(18) 0.032 Uiso 1 1 calc R
C12 C 0.62181(6) 0.4801(3) 1.3180(2) 0.0209(4) Uani 1 1 d .
H12A H 0.6401(3) 0.3634(16) 1.3720(8) 0.025 Uiso 1 1 calc R
H12B H 0.6483(4) 0.5814(14) 1.2847(5) 0.025 Uiso 1 1 calc R
C13 C 0.59537(6) 0.4074(3) 1.1467(2) 0.0185(4) Uani 1 1 d .
H13A H 0.6095(2) 0.2773(19) 1.1146(5) 0.022 Uiso 1 1 calc R
H13B H 0.5591(5) 0.3885(4) 1.1711(4) 0.022 Uiso 1 1 calc R
N1 N 0.64343(5) 0.2398(2) 0.77469(18) 0.0164(3) Uani 1 1 d .
N2 N 0.65364(5) 0.5442(2) 0.92037(17) 0.0152(3) Uani 1 1 d .
H2A H 0.6728(4) 0.647(2) 0.9426(5) 0.018 Uiso 1 1 calc R
N3 N 0.73801(5) -0.0916(2) 0.56015(19) 0.0189(3) Uani 1 1 d .
O1 O 0.78527(4) -0.10379(19) 0.54566(18) 0.0268(3) Uani 1 1 d .
O2 O 0.70882(5) -0.2205(2) 0.5011(2) 0.0355(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0180
-1 0 0 0.0330
-2 1 0 0.1270
-1 1 -1 0.1650
4 -1 0 0.0990
4 1 0 0.1100
-2 0 1 0.1380
-2 -1 0 0.1180
1 -1 -1 0.1660
2 0 1 0.1470
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C1 N1 117.96(14)
N2 C1 C2 119.31(14)
N1 C1 C2 122.73(15)
C3 C2 C1 119.11(16)
C2 C3 C4 118.06(16)
C5 C4 C3 119.67(15)
C5 C4 N3 120.11(14)
C3 C4 N3 120.19(14)
N1 C5 C4 123.53(15)
N2 C6 C7 106.44(12)
N2 C6 C13 109.83(13)
C7 C6 C13 115.42(14)
C8 C7 C6 117.71(14)
C7 C8 C9 117.92(15)
C8 C9 C10 114.96(15)
C11 C10 C9 115.95(16)
C10 C11 C12 118.90(15)
C11 C12 C13 116.56(14)
C6 C13 C12 114.97(15)
C5 N1 C1 116.88(13)
C1 N2 C6 125.22(13)
O2 N3 O1 122.54(14)
O2 N3 C4 119.36(13)
O1 N3 C4 118.10(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.344(2)
C1 N1 1.355(2)
C1 C2 1.419(2)
C2 C3 1.353(2)
C3 C4 1.401(2)
C4 C5 1.382(2)
C4 N3 1.428(2)
C5 N1 1.326(2)
C6 N2 1.462(2)
C6 C7 1.526(2)
C6 C13 1.534(2)
C7 C8 1.525(2)
C8 C9 1.535(3)
C9 C10 1.542(3)
C10 C11 1.522(3)
C11 C12 1.532(2)
C12 C13 1.537(2)
N3 O2 1.2266(18)
N3 O1 1.2369(18)
