#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:18:17 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179659 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/12/4511211.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_4511211
loop_
_publ_author_name
'Draguta, Sergiu'
'Yakovenko, Andrey A.'
'Fonari, Marina S.'
'Timofeeva, Tatiana V.'
_publ_section_title
;
 Unusual Chemical Ratio, Z″ Values, and Polymorphism in Three
 NewN-Methyl Aminopyridine--4-Nitrophenol Adducts
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3423
_journal_paper_doi               10.1021/cg500360f
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C6 H8 N2'
_chemical_formula_sum            'C6 H8 N2'
_chemical_formula_weight         108.14
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.939(5)
_cell_length_b                   8.809(4)
_cell_length_c                   18.406(11)
_cell_measurement_reflns_used    1312
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.21
_cell_measurement_theta_min      3.39
_cell_volume                     1287.2(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.858
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0777
_diffrn_reflns_av_sigmaI/netI    0.1008
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6219
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       0.14(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     80
_refine_ls_number_reflns         974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0881
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1298P)²+0.2633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2434
_refine_ls_wR_factor_ref         0.2695
_reflns_number_gt                603
_reflns_number_total             974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            all_compounds_completed_corrected.cif
_cod_data_source_block           comp_2_273K
_cod_depositor_comments
'Adding full bibliography for 4511210--4511217.cif.'
_cod_original_cell_volume        1287.2(12)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4511211
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.0807(4) 0.5807(4) 0.38886(17) 0.0719(12) Uani 1 1 d .
C2 C 0.1414(4) 0.7210(4) 0.38024(17) 0.0596(12) Uani 1 1 d .
C3 C 0.0633(4) 0.8264(5) 0.3331(2) 0.0697(13) Uani 1 1 d .
H3 H 0.1092 0.9226 0.3266 0.084 Uiso 1 1 calc R
N4 N 0.2828(4) 0.7622(5) 0.41763(18) 0.0773(13) Uani 1 1 d .
H4 H 0.314(6) 0.870(6) 0.407(2) 0.121(18) Uiso 1 1 d .
C5 C -0.0807(5) 0.7854(6) 0.2971(2) 0.0813(15) Uani 1 1 d .
H5 H -0.1326 0.8534 0.2655 0.098 Uiso 1 1 calc R
C6 C -0.1478(5) 0.6446(6) 0.3076(3) 0.0888(16) Uani 1 1 d .
H6 H -0.2479 0.6165 0.2850 0.107 Uiso 1 1 calc R
C7 C -0.0641(5) 0.5455(5) 0.3523(3) 0.0888(16) Uani 1 1 d .
H7 H -0.1085 0.4485 0.3581 0.107 Uiso 1 1 calc R
C8 C 0.3631(7) 0.6645(5) 0.4707(3) 0.1016(18) Uani 1 1 d .
H8A H 0.4129 0.5790 0.4464 0.152 Uiso 1 1 calc R
H8B H 0.2806 0.6294 0.5049 0.152 Uiso 1 1 calc R
H8C H 0.4491 0.7203 0.4958 0.152 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.074(2) 0.057(3) 0.085(2) 0.0008(16) -0.0037(14) -0.0002(16)
C2 0.0625(19) 0.050(3) 0.066(2) -0.0014(17) 0.0034(14) 0.0013(17)
C3 0.072(2) 0.058(3) 0.079(3) 0.0081(18) 0.0042(17) 0.0031(17)
N4 0.076(2) 0.060(3) 0.095(2) 0.0104(18) -0.0147(15) -0.0055(16)
C5 0.078(3) 0.075(4) 0.091(3) -0.001(2) -0.0090(19) 0.019(2)
C6 0.076(3) 0.072(4) 0.118(4) -0.002(3) -0.023(2) 0.005(2)
C7 0.078(3) 0.070(4) 0.119(4) -0.007(2) -0.012(2) -0.011(2)
C8 0.116(3) 0.081(4) 0.108(4) 0.010(3) -0.043(3) -0.001(3)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C7 117.0(3)
N1 C2 N4 118.9(3)
N1 C2 C3 121.4(3)
N4 C2 C3 119.7(4)
C5 C3 C2 119.3(4)
C2 N4 C8 122.9(4)
C6 C5 C3 119.8(4)
C5 C6 C7 118.4(4)
N1 C7 C6 123.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.336(5)
N1 C7 1.368(5)
C2 N4 1.366(5)
C2 C3 1.414(5)
C3 C5 1.370(6)
N4 C8 1.450(5)
C5 C6 1.364(6)
C6 C7 1.371(6)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 N1 1.00(5) 2.06(6) 3.054(5) 170(4) 8_665
