#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:36:15 +0100 (lun 21 de mar de 2016) $
#$Revision: 178474 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/95/4029566.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_4029566
loop_
_publ_author_name
'García-Egido, Eduardo'
'Fernandez-Suarez, Miryam'
'Muñoz, Luis'
_publ_section_title
;
 Synthesis of carbamoyl azides from primary amines and carbon dioxide
 under mild conditions.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2909
_journal_page_last               2911
_journal_paper_doi               10.1021/jo702506v
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C8 H8 N3 O3'
_chemical_formula_weight         194.17
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   7.4210(9)
_cell_length_b                   10.8708(13)
_cell_length_c                   11.1847(13)
_cell_measurement_temperature    293(2)
_cell_volume                     902.29(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5710
_diffrn_reflns_theta_full        28.03
_diffrn_reflns_theta_max         28.03
_diffrn_reflns_theta_min         2.61
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.156442
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          .56
_exptl_crystal_size_mid          .36
_exptl_crystal_size_min          .19
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0583
_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)+(0.0982P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1486
_refine_ls_wR_factor_ref         0.1561
_reflns_number_gt                1741
_reflns_number_total             2143
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702506v-file005.cif
_cod_data_source_block           lmxxxs
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4029566
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'
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
N2 N -0.0998(2) 0.42816(18) 0.17352(17) 0.0340(4) Uani 1 1 d .
O3 O 0.1578(3) 0.37839(18) 0.51679(16) 0.0591(6) Uani 1 1 d .
O1 O 0.0889(3) 0.35501(19) 0.02806(16) 0.0510(5) Uani 1 1 d .
C3 C -0.1329(3) 0.5028(2) 0.2721(2) 0.0333(5) Uani 1 1 d .
N3 N 0.2077(2) 0.4286(2) 0.20195(18) 0.0411(5) Uani 1 1 d .
N1 N -0.3952(3) 0.4353(2) 0.1941(2) 0.0475(6) Uani 1 1 d .
C4 C 0.0238(3) 0.5566(2) 0.3351(2) 0.0381(6) Uani 1 1 d .
H4A H -0.0057 0.5716 0.4183 0.046 Uiso 1 1 calc R
H4B H 0.0576 0.6341 0.2985 0.046 Uiso 1 1 calc R
C6 C 0.0738(3) 0.3990(2) 0.1272(2) 0.0361(5) Uani 1 1 d .
C2 C -0.3159(3) 0.5066(3) 0.2820(3) 0.0449(6) Uani 1 1 d .
H2 H -0.3786 0.5509 0.3397 0.054 Uiso 1 1 calc R
C5 C 0.1792(3) 0.4644(2) 0.3258(2) 0.0358(5) Uani 1 1 d .
H5 H 0.2892 0.5038 0.3556 0.043 Uiso 1 1 calc R
C1 C -0.2640(3) 0.3898(3) 0.1308(2) 0.0421(6) Uani 1 1 d .
H1 H -0.2794 0.3382 0.0652 0.051 Uiso 1 1 calc R
C7 C 0.1394(3) 0.3516(2) 0.4033(2) 0.0377(5) Uani 1 1 d .
O2 O 0.0967(4) 0.2535(2) 0.3661(2) 0.0740(8) Uani 1 1 d .
C8 C 0.1173(6) 0.2821(3) 0.6017(3) 0.0656(9) Uani 1 1 d .
H8A H 0.0418 0.2215 0.5644 0.098 Uiso 1 1 calc R
H8B H 0.0557 0.3167 0.6693 0.098 Uiso 1 1 calc R
H8C H 0.2273 0.2442 0.6278 0.098 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
N2 0.0259(8) 0.0462(10) 0.0300(9) 0.0001(8) -0.0014(7) 0.0001(8)
O3 0.0873(16) 0.0560(13) 0.0339(10) 0.0018(9) -0.0043(10) -0.0133(10)
O1 0.0457(10) 0.0737(12) 0.0338(9) -0.0124(9) 0.0009(8) 0.0001(10)
C3 0.0298(11) 0.0375(11) 0.0325(11) 0.0052(10) 0.0014(9) 0.0038(9)
N3 0.0257(9) 0.0669(15) 0.0308(10) -0.0030(10) 0.0016(8) -0.0004(9)
N1 0.0271(9) 0.0634(14) 0.0519(13) 0.0049(11) -0.0051(9) 0.0018(10)
C4 0.0375(12) 0.0389(12) 0.0379(13) -0.0027(11) 0.0010(10) -0.0004(10)
C6 0.0313(11) 0.0456(12) 0.0313(11) 0.0004(10) 0.0031(9) -0.0021(10)
C2 0.0280(11) 0.0555(15) 0.0511(16) 0.0049(13) 0.0043(11) 0.0055(11)
C5 0.0272(10) 0.0473(13) 0.0330(12) -0.0024(11) -0.0020(9) -0.0036(9)
C1 0.0301(11) 0.0578(16) 0.0385(13) 0.0028(12) -0.0105(10) -0.0059(11)
C7 0.0303(11) 0.0454(13) 0.0374(12) -0.0019(11) -0.0074(9) 0.0050(10)
O2 0.117(2) 0.0498(12) 0.0551(13) -0.0058(10) -0.0145(15) -0.0124(15)
C8 0.085(2) 0.0680(19) 0.0438(16) 0.0147(15) -0.0071(17) -0.0068(19)
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
C1 N2 C3 107.23(19)
C1 N2 C6 127.5(2)
C3 N2 C6 125.30(19)
C7 O3 C8 117.0(2)
C2 C3 N2 104.9(2)
C2 C3 C4 137.1(2)
N2 C3 C4 118.0(2)
C6 N3 C5 123.45(18)
C1 N1 C2 106.4(2)
C3 C4 C5 107.54(19)
C3 C4 H4A 110.2
C5 C4 H4A 110.2
C3 C4 H4B 110.2
C5 C4 H4B 110.2
H4A C4 H4B 108.5
O1 C6 N3 126.7(2)
O1 C6 N2 120.3(2)
N3 C6 N2 113.03(19)
C3 C2 N1 110.4(2)
C3 C2 H2 124.8
N1 C2 H2 124.8
N3 C5 C7 110.7(2)
N3 C5 C4 110.42(19)
C7 C5 C4 109.94(19)
N3 C5 H5 108.6
C7 C5 H5 108.6
C4 C5 H5 108.6
N1 C1 N2 111.0(2)
N1 C1 H1 124.5
N2 C1 H1 124.5
O2 C7 O3 124.6(3)
O2 C7 C5 124.9(2)
O3 C7 C5 110.5(2)
O3 C8 H8A 109.5
O3 C8 H8B 109.5
H8A C8 H8B 109.5
O3 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C1 1.374(3)
N2 C3 1.391(3)
N2 C6 1.424(3)
O3 C7 1.309(3)
O3 C8 1.445(4)
O1 C6 1.213(3)
C3 C2 1.363(3)
C3 C4 1.480(3)
N3 C6 1.338(3)
N3 C5 1.455(3)
N1 C1 1.301(3)
N1 C2 1.383(4)
C4 C5 1.531(3)
C4 H4A 0.9700
C4 H4B 0.9700
C2 H2 0.9300
C5 C7 1.530(4)
C5 H5 0.9800
C1 H1 0.9300
C7 O2 1.188(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
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
C1 N2 C3 C2 -0.9(3)
C6 N2 C3 C2 178.9(2)
C1 N2 C3 C4 -179.9(2)
C6 N2 C3 C4 -0.2(3)
C2 C3 C4 C5 148.7(3)
N2 C3 C4 C5 -32.6(3)
C5 N3 C6 O1 -170.8(2)
C5 N3 C6 N2 11.2(3)
C1 N2 C6 O1 15.0(4)
C3 N2 C6 O1 -164.7(2)
C1 N2 C6 N3 -166.9(2)
C3 N2 C6 N3 13.4(3)
N2 C3 C2 N1 1.0(3)
C4 C3 C2 N1 179.8(3)
C1 N1 C2 C3 -0.7(3)
C6 N3 C5 C7 76.9(3)
C6 N3 C5 C4 -45.1(3)
C3 C4 C5 N3 52.1(2)
C3 C4 C5 C7 -70.4(2)
C2 N1 C1 N2 0.1(3)
C3 N2 C1 N1 0.5(3)
C6 N2 C1 N1 -179.3(2)
C8 O3 C7 O2 -2.1(5)
C8 O3 C7 C5 177.5(3)
N3 C5 C7 O2 -16.1(4)
C4 C5 C7 O2 106.2(3)
N3 C5 C7 O3 164.4(2)
C4 C5 C7 O3 -73.4(3)
