#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:02:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180488 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/57/7215756.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_7215756
loop_
_publ_author_name
'Jones, P. G.'
'Taouss, Christina'
_publ_section_title
;
 Lutidine Adducts of Urea: Molecular Mechanisms for Twinning Effects on
 Cooling
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/c4ce00560k
_journal_year                    2014
_chemical_formula_sum            'C9 H17 N5 O2'
_chemical_formula_weight         227.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m 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            4
_cell_length_a                   8.0772(3)
_cell_length_b                   7.2986(3)
_cell_length_c                   20.4169(7)
_cell_measurement_reflns_used    10235
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3070
_cell_measurement_theta_min      2.7030
_cell_volume                     1203.62(8)
_computing_cell_refinement
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_data_collection
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_data_reduction
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0108
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            38287
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         29.37
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0408
_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)+(0.0519P)²+0.5129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                1517
_reflns_number_total             1710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00560k1.cif
_cod_data_source_block           laufen
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1203.64(8)
_cod_database_code               7215756
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N11 N 0.41604(16) 0.7500 0.46732(6) 0.0189(3) Uani 1 2 d S
C12 C 0.4151(2) 0.7500 0.53317(7) 0.0240(3) Uani 1 2 d S
C13 C 0.5632(3) 0.7500 0.56923(8) 0.0316(4) Uani 1 2 d S
H13 H 0.5607 0.7500 0.6157 0.038 Uiso 1 2 calc SR
C14 C 0.7119(2) 0.7500 0.53631(9) 0.0300(4) Uani 1 2 d S
H14 H 0.8132 0.7500 0.5599 0.036 Uiso 1 2 calc SR
C15 C 0.7127(2) 0.7500 0.46882(9) 0.0259(4) Uani 1 2 d S
H15 H 0.8142 0.7500 0.4453 0.031 Uiso 1 2 calc SR
C16 C 0.56272(19) 0.7500 0.43587(8) 0.0208(3) Uani 1 2 d S
C17 C 0.2491(3) 0.7500 0.56554(9) 0.0382(5) Uani 1 2 d S
H17A H 0.2152 0.8765 0.5745 0.057 Uiso 0.50 1 calc PR
H17B H 0.2554 0.6817 0.6068 0.057 Uiso 0.50 1 calc PR
H17C H 0.1679 0.6919 0.5366 0.057 Uiso 0.50 1 calc PR
C18 C 0.5565(2) 0.7500 0.36216(8) 0.0335(4) Uani 1 2 d S
H18A H 0.4979 0.6405 0.3469 0.050 Uiso 1 1 d R
H18B H 0.6695 0.7500 0.3446 0.050 Uiso 1 2 d SR
C1 C 0.07513(17) 0.7500 0.35383(7) 0.0165(3) Uani 1 2 d S
N1 N 0.12769(12) 0.59321(13) 0.38207(5) 0.0215(2) Uani 1 1 d .
H01 H 0.2071(19) 0.601(2) 0.4107(7) 0.029(4) Uiso 1 1 d .
H02 H 0.1024(18) 0.489(2) 0.3636(7) 0.028(4) Uiso 1 1 d .
O1 O -0.02090(14) 0.7500 0.30616(5) 0.0210(3) Uani 1 2 d S
C2 C -0.08185(17) 0.2500 0.27760(7) 0.0145(3) Uani 1 2 d S
N2 N -0.15430(12) 0.40715(13) 0.25925(5) 0.0206(2) Uani 1 1 d .
H03 H -0.2498(19) 0.402(2) 0.2388(7) 0.030(4) Uiso 1 1 d .
H04 H -0.1140(18) 0.511(2) 0.2732(6) 0.026(3) Uiso 1 1 d .
O2 O 0.05114(12) 0.2500 0.31004(5) 0.0163(2) Uani 1 2 d S
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
C12 N11 C16 118.77(13) . .
N11 C12 C13 121.30(16) . .
N11 C12 C17 116.55(15) . .
C13 C12 C17 122.15(15) . .
C14 C13 C12 119.15(15) . .
C13 C14 C15 119.52(16) . .
C14 C15 C16 118.76(16) . .
N11 C16 C15 122.50(15) . .
N11 C16 C18 116.56(14) . .
C15 C16 C18 120.94(15) . .
O1 C1 N1 122.01(6) . .
O1 C1 N1 122.01(6) . 7_575
N1 C1 N1 115.94(13) . 7_575
O2 C2 N2 121.20(6) . 7_565
O2 C2 N2 121.20(6) . .
N2 C2 N2 117.59(13) 7_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.344(2) .
N11 C16 1.348(2) .
C12 C13 1.404(3) .
C12 C17 1.495(2) .
C13 C14 1.376(3) .
C14 C15 1.378(3) .
C15 C16 1.386(2) .
C16 C18 1.506(2) .
C1 O1 1.2445(18) .
C1 N1 1.3498(11) .
C1 N1 1.3499(12) 7_575
C2 O2 1.2621(17) .
C2 N2 1.3410(11) 7_565
C2 N2 1.3410(11) .
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
N1 H01 N11 0.869(15) 2.318(16) 3.1248(15) 154.4(13) .
N1 H02 O2 0.871(16) 2.102(16) 2.9698(11) 174.2(13) .
N2 H03 O2 0.878(15) 2.192(16) 2.9963(13) 152.1(14) 6_556
N2 H04 O1 0.870(15) 2.018(16) 2.8879(11) 179.5(13) .
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
C16 N11 C12 C13 0.0
C16 N11 C12 C17 180.0
N11 C12 C13 C14 0.0
C17 C12 C13 C14 180.0
C12 C13 C14 C15 0.0
C13 C14 C15 C16 0.0
C12 N11 C16 C15 0.000(1)
C12 N11 C16 C18 180.0
C14 C15 C16 N11 0.000(1)
C14 C15 C16 C18 180.0
