#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:00:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180055 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/01/7050183.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_7050183
loop_
_publ_author_name
'Isabel Iriepa'
'F. Javier Villasante'
'Enrique Gálvez'
'Juana Bellanato'
'Avelino Martín'
'Pilar Gómez-Sal'
_publ_section_title
;
 Synthesis, spectroscopic and crystallographic study of some carbamates
 from an azabicyclic chloroformate and primary heterocyclic amines
;
_journal_issue                   5
_journal_name_full               'New J. Chem.'
_journal_page_first              618
_journal_page_last               624
_journal_paper_doi               10.1039/b309065e
_journal_volume                  28
_journal_year                    2004
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H22 N4 O2'
_chemical_formula_structural     'C17 N4 O2 H22'
_chemical_formula_sum            'C17 H22 N4 O2'
_chemical_formula_weight         314.38
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core2.1beta.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1beta3
_audit_creation_date             2000-03-10T11:19:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 106.640(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.644(3)
_cell_length_b                   14.574(5)
_cell_length_c                   17.816(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      6
_cell_measurement_wavelength     0.71073
_cell_volume                     3394.3(16)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega-theta scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.4211E-2
_diffrn_orient_matrix_UB_12      -0.40253E-1
_diffrn_orient_matrix_UB_13      -0.44403E-1
_diffrn_orient_matrix_UB_21      0.59624E-1
_diffrn_orient_matrix_UB_22      0.36487E-1
_diffrn_orient_matrix_UB_23      -0.5616E-2
_diffrn_orient_matrix_UB_31      0.48012E-1
_diffrn_orient_matrix_UB_32      -0.04175
_diffrn_orient_matrix_UB_33      0.37916E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_sigmaI/netI    0.1273
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6212
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.04
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.227
_refine_ls_R_factor_gt           0.0846
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1641P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2287
_refine_ls_wR_factor_ref         0.3129
_reflns_number_gt                2376
_reflns_number_total             5948
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b309065e.txt
_cod_data_source_block           iic2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1641P)^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^)+(0.1641P)^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      'P 21/c'
_cod_database_code               7050183
#BEGIN Tags that were not found in dictionaries:
_diffrn_standards_decay_corr_max 1.025
_diffrn_standards_decay_corr_min 0.965
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1394(5) 0.7450(3) 0.7030(3) 0.0894(18) Uani 1 1 d . . .
O2 O 0.1215(4) 0.5922(3) 0.6780(3) 0.0720(15) Uani 1 1 d . . .
N1 N 0.2662(4) 0.7513(3) 0.5187(3) 0.0551(14) Uani 1 1 d . . .
N2 N 0.2147(4) 0.8411(3) 0.6015(3) 0.0518(14) Uani 1 1 d . . .
H1 H 0.1967 0.8474 0.6329 0.069 Uiso 1 1 d R . .
N3 N 0.1863(4) 0.6785(3) 0.6028(3) 0.0504(14) Uani 1 1 d . . .
H2 H 0.1876 0.6196 0.5774 0.064 Uiso 1 1 d R . .
N4 N -0.0955(5) 0.4753(5) 0.7719(4) 0.0764(19) Uani 1 1 d . . .
C1 C 0.2612(5) 0.9005(4) 0.5598(4) 0.0525(16) Uani 1 1 d . . .
C2 C 0.2807(5) 0.9928(5) 0.5635(5) 0.0651(19) Uani 1 1 d . . .
H3 H 0.2633 1.0303 0.6022 0.08 Uiso 1 1 d R . .
C3 C 0.3308(6) 1.0275(5) 0.5124(5) 0.079(2) Uani 1 1 d . . .
H4 H 0.3433 1.0922 0.5127 0.08 Uiso 1 1 d R . .
C4 C 0.3599(6) 0.9701(5) 0.4600(5) 0.078(2) Uani 1 1 d . . .
H5 H 0.393 0.9972 0.4246 0.08 Uiso 1 1 d R . .
C5 C 0.3420(6) 0.8792(5) 0.4570(4) 0.071(2) Uani 1 1 d . . .
H6 H 0.3649 0.8402 0.4221 0.08 Uiso 1 1 d R . .
C6 C 0.2911(5) 0.8427(4) 0.5085(4) 0.0498(16) Uani 1 1 d . . .
C7 C 0.2213(5) 0.7557(4) 0.5748(4) 0.0477(16) Uani 1 1 d . . .
C8 C 0.1484(6) 0.6782(5) 0.6646(4) 0.0642(19) Uani 1 1 d . . .
C9 C 0.0747(5) 0.5819(5) 0.7430(4) 0.0591(19) Uani 1 1 d . . .
H7 H 0.1121 0.6169 0.7878 0.08 Uiso 1 1 d R . .
C10 C 0.0853(6) 0.4827(5) 0.7663(5) 0.080(2) Uani 1 1 d . . .
H8 H 0.0644 0.4504 0.7173 0.08 Uiso 1 1 d R . .
H9 H 0.1548 0.4656 0.7924 0.08 Uiso 1 1 d R . .
C11 C 0.0123(5) 0.4508(5) 0.8132(4) 0.066(2) Uani 1 1 d . . .
H10 H 0.0165 0.3853 0.8175 0.08 Uiso 1 1 d R . .
C12 C 0.0387(6) 0.4886(6) 0.8934(4) 0.081(2) Uani 1 1 d . . .
H11 H -0.0023 0.4576 0.9212 0.08 Uiso 1 1 d R . .
H12 H 0.1093 0.4753 0.9198 0.08 Uiso 1 1 d R . .
C13 C 0.0212(6) 0.5902(6) 0.8982(4) 0.082(2) Uani 1 1 d . . .
H13 H 0.0209 0.6056 0.9505 0.08 Uiso 1 1 d R . .
H14 H 0.0774 0.622 0.8876 0.08 Uiso 1 1 d R . .
C14 C -0.0798(7) 0.6193(6) 0.8429(5) 0.088(3) Uani 1 1 d . . .
H15 H -0.0756 0.6842 0.8356 0.08 Uiso 1 1 d R . .
H16 H -0.1349 0.6084 0.8654 0.08 Uiso 1 1 d R . .
C15 C -0.1018(6) 0.5740(6) 0.7640(5) 0.083(2) Uani 1 1 d . . .
H17 H -0.1718 0.5884 0.7367 0.08 Uiso 1 1 d R . .
C16 C -0.0333(6) 0.6103(6) 0.7135(4) 0.079(2) Uani 1 1 d . . .
H18 H -0.0359 0.6761 0.7136 0.08 Uiso 1 1 d R . .
H19 H -0.0604 0.59 0.6602 0.08 Uiso 1 1 d R . .
C17 C -0.1396(8) 0.4288(7) 0.7011(5) 0.119(4) Uani 1 1 d . . .
H20 H -0.1313 0.3642 0.7107 0.08 Uiso 1 1 d R . .
H21 H -0.106 0.4463 0.6627 0.08 Uiso 1 1 d R . .
H22 H -0.2113 0.4432 0.6819 0.08 Uiso 1 1 d R . .
O3 O 0.4323(4) 0.5027(3) 0.4043(3) 0.0679(14) Uani 1 1 d . . .
O4 O 0.4420(3) 0.6575(3) 0.4159(2) 0.0559(12) Uani 1 1 d . . .
N5 N 0.2110(4) 0.5208(3) 0.5201(3) 0.0496(13) Uani 1 1 d . . .
N6 N 0.2909(4) 0.4232(3) 0.4619(3) 0.0508(13) Uani 1 1 d . . .
H23 H 0.3368 0.402 0.4386 0.08 Uiso 1 1 d R . .
N7 N 0.3414(4) 0.5822(3) 0.4734(3) 0.0499(13) Uani 1 1 d . . .
H24 H 0.3195 0.6428 0.49 0.154 Uiso 1 1 d R . .
N8 N 0.5316(4) 0.7687(4) 0.2270(3) 0.0541(14) Uani 1 1 d . . .
C18 C 0.2145(5) 0.3724(4) 0.4806(3) 0.0458(15) Uani 1 1 d . . .
C19 C 0.1849(5) 0.2817(5) 0.4673(4) 0.0594(18) Uani 1 1 d . . .
H25 H 0.2212 0.24 0.4433 0.08 Uiso 1 1 d R . .
C20 C 0.1023(6) 0.2550(5) 0.4920(4) 0.067(2) Uani 1 1 d . . .
H26 H 0.078 0.1931 0.483 0.08 Uiso 1 1 d R . .
C21 C 0.0520(6) 0.3177(5) 0.5289(4) 0.069(2) Uani 1 1 d . . .
H27 H -0.0035 0.2954 0.5469 0.08 Uiso 1 1 d R . .
C22 C 0.0813(5) 0.4076(5) 0.5409(4) 0.0556(17) Uani 1 1 d . . .
H28 H 0.044 0.4499 0.5636 0.08 Uiso 1 1 d R . .
C23 C 0.1655(5) 0.4352(4) 0.5175(3) 0.0470(15) Uani 1 1 d . . .
C24 C 0.2830(5) 0.5090(4) 0.4853(3) 0.0442(15) Uani 1 1 d . . .
C25 C 0.4087(5) 0.5739(5) 0.4286(4) 0.0543(17) Uani 1 1 d . . .
C26 C 0.5004(5) 0.6586(4) 0.3584(3) 0.0500(16) Uani 1 1 d . . .
H29 H 0.5456 0.6068 0.3661 0.08 Uiso 1 1 d R . .
C27 C 0.5626(5) 0.7453(4) 0.3713(4) 0.0569(18) Uani 1 1 d . . .
H30 H 0.6161 0.74 0.4199 0.08 Uiso 1 1 d R . .
H31 H 0.5186 0.7949 0.3764 0.08 Uiso 1 1 d R . .
C28 C 0.6119(5) 0.7649(5) 0.3037(4) 0.0584(18) Uani 1 1 d . . .
H32 H 0.6417 0.825 0.3131 0.08 Uiso 1 1 d R . .
C29 C 0.6911(5) 0.6991(6) 0.2960(5) 0.076(2) Uani 1 1 d . . .
H33 H 0.7434 0.6949 0.3454 0.08 Uiso 1 1 d R . .
H34 H 0.722 0.7228 0.258 0.08 Uiso 1 1 d R . .
C30 C 0.6519(7) 0.6041(6) 0.2682(5) 0.087(3) Uani 1 1 d . . .
H35 H 0.702 0.5695 0.2517 0.08 Uiso 1 1 d R . .
H36 H 0.6395 0.5731 0.3121 0.08 Uiso 1 1 d R . .
C31 C 0.5539(7) 0.6087(5) 0.2020(5) 0.078(2) Uani 1 1 d . . .
H37 H 0.57 0.6219 0.1541 0.08 Uiso 1 1 d R . .
H38 H 0.5209 0.5499 0.1963 0.08 Uiso 1 1 d R . .
C32 C 0.4787(5) 0.6801(5) 0.2129(4) 0.0559(18) Uani 1 1 d . . .
H39 H 0.4252 0.6851 0.1643 0.08 Uiso 1 1 d R . .
C33 C 0.4278(5) 0.6547(5) 0.2769(4) 0.0585(18) Uani 1 1 d . . .
H40 H 0.3978 0.5947 0.2673 0.08 Uiso 1 1 d R . .
H41 H 0.3737 0.698 0.2739 0.08 Uiso 1 1 d R . .
C34 C 0.4631(6) 0.8469(5) 0.2177(5) 0.080(2) Uani 1 1 d . . .
H42 H 0.5039 0.9016 0.2275 0.08 Uiso 1 1 d R . .
H43 H 0.4169 0.8489 0.1655 0.08 Uiso 1 1 d R . .
H44 H 0.4244 0.8425 0.2549 0.08 Uiso 1 1 d R . .
C100 C 0.4092(4) 0.2845(4) 0.4143(3) 0.0423(15) 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
3 1 2
6 1 -5
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
C8 O2 C9 115.6(5) . . ?
C7 N1 C6 103.6(5) . . ?
C7 N2 C1 107.3(5) . . ?
C8 N3 C7 123.8(6) . . ?
C17 N4 C15 113.2(7) . . ?
C17 N4 C11 115.9(8) . . ?
C15 N4 C11 108.0(6) . . ?
C2 C1 C6 122.6(6) . . ?
C2 C1 N2 133.6(6) . . ?
C6 C1 N2 103.7(5) . . ?
C1 C2 C3 116.9(7) . . ?
C2 C3 C4 120.8(7) . . ?
C5 C4 C3 122.3(7) . . ?
C4 C5 C6 117.8(7) . . ?
C1 C6 N1 111.3(5) . . ?
C1 C6 C5 119.6(6) . . ?
N1 C6 C5 129.1(6) . . ?
N1 C7 N2 114.0(5) . . ?
N1 C7 N3 121.5(5) . . ?
N2 C7 N3 124.4(5) . . ?
O1 C8 N3 125.7(7) . . ?
O1 C8 O2 124.7(6) . . ?
N3 C8 O2 109.7(6) . . ?
C16 C9 O2 107.6(6) . . ?
C16 C9 C10 112.1(6) . . ?
O2 C9 C10 106.5(5) . . ?
C9 C10 C11 114.5(6) . . ?
C12 C11 N4 108.8(6) . . ?
C12 C11 C10 113.3(7) . . ?
N4 C11 C10 111.1(6) . . ?
C11 C12 C13 115.1(6) . . ?
C12 C13 C14 111.7(7) . . ?
C13 C14 C15 112.8(7) . . ?
N4 C15 C14 110.9(7) . . ?
N4 C15 C16 111.4(7) . . ?
C14 C15 C16 113.3(7) . . ?
C9 C16 C15 113.6(6) . . ?
C25 O4 C26 114.0(5) . . ?
C24 N5 C23 104.7(5) . . ?
C24 N6 C18 106.9(5) . . ?
C25 N7 C24 121.9(5) . . ?
C34 N8 C32 113.6(6) . . ?
C34 N8 C28 114.5(6) . . ?
C32 N8 C28 108.8(5) . . ?
C19 C18 N6 132.0(6) . . ?
C19 C18 C23 123.3(6) . . ?
N6 C18 C23 104.7(5) . . ?
C20 C19 C18 116.1(6) . . ?
C19 C20 C21 121.1(6) . . ?
C22 C21 C20 122.2(7) . . ?
C21 C22 C23 117.4(6) . . ?
N5 C23 C22 130.6(6) . . ?
N5 C23 C18 109.5(5) . . ?
C22 C23 C18 119.8(6) . . ?
N5 C24 N6 114.1(5) . . ?
N5 C24 N7 120.8(5) . . ?
N6 C24 N7 125.0(5) . . ?
O3 C25 O4 125.6(5) . . ?
O3 C25 N7 125.0(6) . . ?
O4 C25 N7 109.3(6) . . ?
O4 C26 C27 107.4(5) . . ?
O4 C26 C33 109.5(5) . . ?
C27 C26 C33 111.5(5) . . ?
C26 C27 C28 112.6(5) . . ?
C29 C28 N8 107.7(6) . . ?
C29 C28 C27 116.0(6) . . ?
N8 C28 C27 110.4(5) . . ?
C28 C29 C30 115.1(6) . . ?
C29 C30 C31 111.4(6) . . ?
C30 C31 C32 114.3(6) . . ?
N8 C32 C31 108.0(5) . . ?
N8 C32 C33 112.9(5) . . ?
C31 C32 C33 113.3(6) . . ?
C26 C33 C32 113.1(5) . . ?
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 C8 1.217(7) . ?
O2 C8 1.346(8) . ?
O2 C9 1.483(7) . ?
N1 C7 1.315(7) . ?
N1 C6 1.399(7) . ?
N2 C7 1.344(7) . ?
N2 C1 1.405(7) . ?
N3 C8 1.344(7) . ?
N3 C7 1.371(7) . ?
N4 C17 1.406(10) . ?
N4 C15 1.445(10) . ?
N4 C11 1.488(9) . ?
C1 C2 1.370(9) . ?
C1 C6 1.387(8) . ?
C2 C3 1.381(10) . ?
C3 C4 1.393(10) . ?
C4 C5 1.345(9) . ?
C5 C6 1.404(8) . ?
C9 C16 1.475(9) . ?
C9 C10 1.501(9) . ?
C10 C11 1.542(9) . ?
C11 C12 1.476(10) . ?
C12 C13 1.506(10) . ?
C13 C14 1.507(11) . ?
C14 C15 1.503(11) . ?
C15 C16 1.564(10) . ?
O3 C25 1.203(7) . ?
O4 C25 1.342(7) . ?
O4 C26 1.467(6) . ?
N5 C24 1.315(7) . ?
N5 C23 1.388(7) . ?
N6 C24 1.332(7) . ?
N6 C18 1.394(7) . ?
N7 C25 1.382(7) . ?
N7 C24 1.384(7) . ?
N8 C34 1.453(8) . ?
N8 C32 1.466(8) . ?
N8 C28 1.487(8) . ?
C18 C19 1.382(8) . ?
C18 C23 1.404(8) . ?
C19 C20 1.378(9) . ?
C20 C21 1.412(10) . ?
C21 C22 1.368(9) . ?
C22 C23 1.389(8) . ?
C26 C27 1.503(8) . ?
C26 C33 1.506(8) . ?
C27 C28 1.565(8) . ?
C28 C29 1.480(9) . ?
C29 C30 1.515(10) . ?
C30 C31 1.511(11) . ?
C31 C32 1.513(9) . ?
C32 C33 1.541(8) . ?
