#------------------------------------------------------------------------------
#$Date: 2016-09-06 17:33:39 +0200 (mar 06 de sep de 2016) $
#$Revision: 186217 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/64/7226482.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_7226482
loop_
_publ_author_name
'Singh, Anoop S.'
'Kumar, Dhananjay'
'Mishra, Nidhi'
'Tiwari, Vinod K.'
_publ_section_title
;
 An efficient one-pot synthesis of N,N′-disubstituted ureas and
 carbamates from N-acylbenzotriazoles
;
_journal_issue                   87
_journal_name_full               'RSC Adv.'
_journal_page_first              84512
_journal_paper_doi               10.1039/C6RA14131E
_journal_volume                  6
_journal_year                    2016
_chemical_formula_moiety         'C7 H5 N O2'
_chemical_formula_sum            'C7 H5 N O2'
_chemical_formula_weight         135.12
_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
_audit_update_record
;
2016-05-27 deposited with the CCDC.
2016-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4436(14)
_cell_length_b                   6.641(2)
_cell_length_c                   20.957(6)
_cell_measurement_reflns_used    1585
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.94
_cell_measurement_theta_min      3.22
_cell_volume                     618.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      273(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0159
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3269
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0518P)²+0.0364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                1322
_reflns_number_total             1471
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra14131e2.cif
_cod_data_source_block           compound_5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        618.5(3)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7226482
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
O1 O 0.3521(2) 0.81059(15) 0.12378(5) 0.0545(3) Uani 1 1 d .
N1 N 0.2463(3) 0.5733(2) 0.19359(6) 0.0535(3) Uani 1 1 d .
H1 H 0.1701 0.5119 0.2259 0.064 Uiso 1 1 calc R
C1 C 0.5125(3) 0.63982(19) 0.10785(7) 0.0449(3) Uani 1 1 d .
C2 C 0.4491(3) 0.4899(2) 0.15092(7) 0.0455(3) Uani 1 1 d .
O2 O 0.0193(3) 0.8862(2) 0.20110(7) 0.0813(4) Uani 1 1 d .
C3 C 0.5786(4) 0.3018(2) 0.14505(8) 0.0584(4) Uani 1 1 d .
H3 H 0.5365 0.1985 0.1737 0.070 Uiso 1 1 calc R
C4 C 0.1861(4) 0.7650(2) 0.17690(7) 0.0552(4) Uani 1 1 d .
C5 C 0.7734(4) 0.2750(3) 0.09455(9) 0.0673(5) Uani 1 1 d .
H5 H 0.8658 0.1505 0.0892 0.081 Uiso 1 1 calc R
C6 C 0.7049(4) 0.6147(3) 0.05750(7) 0.0583(4) Uani 1 1 d .
H6 H 0.7453 0.7180 0.0288 0.070 Uiso 1 1 calc R
C7 C 0.8356(4) 0.4268(3) 0.05179(9) 0.0679(5) Uani 1 1 d .
H7 H 0.9683 0.4024 0.0184 0.081 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
O1 0.0623(6) 0.0469(5) 0.0544(6) 0.0040(4) 0.0068(5) 0.0054(5)
N1 0.0593(7) 0.0579(7) 0.0433(6) 0.0039(5) 0.0064(6) -0.0051(6)
C1 0.0437(7) 0.0455(6) 0.0456(7) -0.0004(5) -0.0030(5) -0.0027(5)
C2 0.0439(6) 0.0487(7) 0.0438(7) -0.0015(6) -0.0061(6) -0.0069(6)
O2 0.0926(9) 0.0820(8) 0.0693(8) -0.0149(6) 0.0140(7) 0.0258(8)
C3 0.0632(9) 0.0443(7) 0.0676(10) 0.0026(7) -0.0151(8) -0.0043(7)
C4 0.0595(8) 0.0581(8) 0.0478(8) -0.0069(6) 0.0017(7) 0.0045(7)
C5 0.0592(9) 0.0580(9) 0.0848(12) -0.0206(9) -0.0140(9) 0.0119(8)
C6 0.0522(8) 0.0708(10) 0.0520(8) 0.0043(7) 0.0050(7) -0.0008(8)
C7 0.0508(8) 0.0890(13) 0.0639(10) -0.0210(9) 0.0019(8) 0.0066(9)
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
C4 O1 C1 107.04(11)
C4 N1 C2 109.86(12)
C4 N1 H1 125.1
C2 N1 H1 125.1
C6 C1 C2 123.12(14)
C6 C1 O1 127.54(13)
C2 C1 O1 109.34(12)
C1 C2 C3 120.80(14)
C1 C2 N1 105.51(12)
C3 C2 N1 133.68(13)
C5 C3 C2 116.53(15)
C5 C3 H3 121.7
C2 C3 H3 121.7
O2 C4 N1 130.05(17)
O2 C4 O1 121.70(16)
N1 C4 O1 108.25(13)
C7 C5 C3 122.08(16)
C7 C5 H5 119.0
C3 C5 H5 119.0
C1 C6 C7 116.09(16)
C1 C6 H6 122.0
C7 C6 H6 122.0
C5 C7 C6 121.37(16)
C5 C7 H7 119.3
C6 C7 H7 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.3694(19)
O1 C1 1.3802(16)
N1 C4 1.347(2)
N1 C2 1.3854(18)
N1 H1 0.8600
C1 C6 1.368(2)
C1 C2 1.373(2)
C2 C3 1.381(2)
O2 C4 1.2059(19)
C3 C5 1.379(3)
C3 H3 0.9300
C5 C7 1.377(3)
C5 H5 0.9300
C6 C7 1.381(3)
C6 H6 0.9300
C7 H7 0.9300
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
C4 O1 C1 C6 178.96(15)
C4 O1 C1 C2 -0.51(16)
C6 C1 C2 C3 -0.4(2)
O1 C1 C2 C3 179.13(12)
C6 C1 C2 N1 -179.56(14)
O1 C1 C2 N1 -0.06(15)
C4 N1 C2 C1 0.63(16)
C4 N1 C2 C3 -178.41(16)
C1 C2 C3 C5 0.5(2)
N1 C2 C3 C5 179.42(15)
C2 N1 C4 O2 178.78(17)
C2 N1 C4 O1 -0.96(17)
C1 O1 C4 O2 -178.87(15)
C1 O1 C4 N1 0.90(16)
C2 C3 C5 C7 -0.4(2)
C2 C1 C6 C7 0.0(2)
O1 C1 C6 C7 -179.35(14)
C3 C5 C7 C6 0.1(3)
C1 C6 C7 C5 0.1(2)
