#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/72/1507291.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_1507291
loop_
_publ_author_name
'Ripka, Amy S.'
'Díaz, David D'
'Sharpless, K. Barry'
'Finn, M. G.'
_publ_section_title
;
 First practical synthesis of formamidine ureas and derivatives.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              1531
_journal_page_last               1533
_journal_paper_doi               10.1021/ol034287r
_journal_volume                  5
_journal_year                    2003
_chemical_formula_moiety         'C22 H32 Cl2 N6 O2'
_chemical_formula_sum            'C11 H16 Cl N3 O'
_chemical_formula_weight         241.72
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             'Mon Dec 17 15:50:32 2002'
_audit_creation_method           'from TEXRAY.INF file'
_cell_angle_alpha                106.79(4)
_cell_angle_beta                 94.99(5)
_cell_angle_gamma                84.92(4)
_cell_formula_units_Z            4
_cell_length_a                   10.496(6)
_cell_length_b                   13.985(6)
_cell_length_c                   9.237(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173.2
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      25.0
_cell_volume                     1290.3(12)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        teXsan
_computing_publication_material  teXsan
_computing_structure_refinement  teXsan
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      173.2
_diffrn_measurement_device       AFC6S
_diffrn_measurement_method       'omega/2-theta scans'
_diffrn_orient_matrix_UB_11      -0.02073
_diffrn_orient_matrix_UB_12      -0.06674
_diffrn_orient_matrix_UB_13      -0.07009
_diffrn_orient_matrix_UB_21      -0.00612
_diffrn_orient_matrix_UB_22      0.02868
_diffrn_orient_matrix_UB_23      -0.08797
_diffrn_orient_matrix_UB_31      0.09338
_diffrn_orient_matrix_UB_32      -0.01804
_diffrn_orient_matrix_UB_33      -0.01383
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoKalpha
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  2.89
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3829
_diffrn_reflns_reduction_process 'texsan PROCESS'
_diffrn_reflns_theta_max         23.00
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             512.00
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.38
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   none
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.608
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     289
_refine_ls_number_reflns         2297
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0467
_refine_ls_shift/esd_max         0.0010
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_obs         0.0620
_reflns_number_observed          2297
_reflns_number_total             3597
_reflns_observed_criterion       3.00
_cod_data_source_file            ol034287rsi20030218_083912.cif
_cod_data_source_block           C11H16ClN3O
_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        1290(1)
_cod_original_sg_symbol_H-M      'P -1       '
_cod_original_formula_sum        'C11 H16 Cl N3 O '
_cod_database_code               1507291
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   -y,   -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
Cl(1) 1.8352(1) -0.13707(8) 1.0874(1) 0.0299(3) Uij
Cl(2) 2.3602(1) -0.48812(8) 0.8038(1) 0.0314(3) Uij
O(1) 1.7632(3) -0.1868(2) 0.6730(4) 0.043(1) Uij
O(2) 2.3303(3) -0.2430(2) 0.6544(4) 0.039(1) Uij
N(1) 1.7306(4) -0.3050(3) 0.4488(4) 0.031(1) Uij
N(2) 1.6276(3) -0.3108(3) 0.6598(4) 0.025(1) Uij
N(3) 1.5463(3) -0.3120(3) 0.8869(4) 0.026(1) Uij
N(4) 2.2802(3) -0.0760(3) 0.7050(4) 0.033(1) Uij
N(5) 2.1474(3) -0.1773(3) 0.7792(4) 0.028(1) Uij
N(6) 2.0544(3) -0.2726(3) 0.9051(4) 0.027(1) Uij
C(1) 1.7135(4) -0.2617(4) 0.5953(5) 0.030(1) Uij
C(2) 1.6203(4) -0.2773(3) 0.8112(5) 0.026(1) Uij
C(3) 1.5508(4) -0.2763(3) 1.0541(5) 0.027(1) Uij
C(4) 1.4303(4) -0.2129(3) 1.1100(5) 0.026(1) Uij
C(5) 1.4005(5) -0.1226(4) 1.0782(5) 0.040(2) Uij
C(6) 1.2904(6) -0.0637(4) 1.1357(6) 0.050(2) Uij
C(7) 1.2132(5) -0.0965(5) 1.2208(6) 0.055(2) Uij
C(8) 1.2420(5) -0.1862(4) 1.2521(6) 0.049(2) Uij
C(9) 1.3505(4) -0.2458(4) 1.1963(5) 0.036(1) Uij
C(10) 1.8096(5) -0.2556(4) 0.3717(5) 0.049(2) Uij
C(11) 1.5532(4) -0.3922(3) 0.5649(5) 0.030(1) Uij
C(12) 2.2609(4) -0.1682(4) 0.7073(5) 0.028(1) Uij
C(13) 2.1441(4) -0.2582(3) 0.8283(5) 0.026(1) Uij
C(14) 2.0554(4) -0.3649(3) 0.9537(5) 0.029(1) Uij
C(15) 1.9629(4) -0.4365(3) 0.8540(5) 0.026(1) Uij
C(16) 1.8414(4) -0.4448(3) 0.8981(5) 0.030(1) Uij
C(17) 1.7578(4) -0.5105(4) 0.8045(6) 0.036(1) Uij
C(18) 1.7942(5) -0.5707(4) 0.6646(6) 0.038(2) Uij
C(19) 1.9154(5) -0.5636(4) 0.6203(5) 0.044(2) Uij
C(20) 1.9992(5) -0.4983(4) 0.7130(5) 0.038(2) Uij
C(21) 2.3930(5) -0.0575(4) 0.6392(6) 0.047(2) Uij
C(22) 2.0420(4) -0.0996(4) 0.8053(6) 0.038(1) Uij
H(1) 1.9773 -0.2223 0.9388 0.0450 Uij
H(2) 2.2244 -0.0175 0.7600 0.0450 Uij
H(3) 1.4947 -0.3725 0.8289 0.0450 Uij
H(4) 1.6912 -0.3724 0.3773 0.0450 Uij
H(5) 2.2184 -0.3079 0.8034 0.0450 Uij
H(6) 2.1528 -0.4013 0.9416 0.0450 Uij
H(7) 2.0282 -0.3405 1.0673 0.0450 Uij
H(8) 1.8148 -0.3952 1.0068 0.0450 Uij
H(9) 1.6605 -0.5161 0.8353 0.0450 Uij
H(10) 1.7271 -0.6163 0.5919 0.0450 Uij
H(11) 1.9467 -0.6177 0.5063 0.0450 Uij
H(12) 2.1006 -0.4890 0.6978 0.0450 Uij
H(13) 1.6871 -0.2207 0.8680 0.0450 Uij
H(14) 1.3775 -0.3182 1.2327 0.0450 Uij
H(15) 1.1634 -0.2207 1.2979 0.0450 Uij
H(16) 1.5682 -0.3347 1.1004 0.0450 Uij
H(17) 1.6440 -0.2364 1.0967 0.0450 Uij
H(18) 1.5014 -0.4133 0.6214 0.0450 Uij
H(19) 1.5079 -0.3720 0.4780 0.0450 Uij
H(20) 1.6055 -0.4553 0.5129 0.0450 Uij
H(21) 2.0393 -0.0636 0.7246 0.0450 Uij
H(22) 1.9642 -0.1300 0.7958 0.0450 Uij
H(23) 2.0515 -0.0483 0.9097 0.0450 Uij
H(24) 2.3984 -0.1098 0.5402 0.0450 Uij
H(25) 2.4764 -0.0635 0.6898 0.0450 Uij
H(26) 2.3799 -0.0140 0.5980 0.0450 Uij
H(27) 1.8818 -0.2998 0.3317 0.0570 Uij
H(28) 1.7613 -0.2381 0.2901 0.0570 Uij
H(29) 1.8418 -0.1964 0.4409 0.0570 Uij
H(30) 1.4566 -0.0999 1.0168 0.0481 Uij
H(31) 1.2708 0.0007 1.1134 0.0623 Uij
H(32) 1.1371 -0.0555 1.2606 0.0651 Uij
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 44 0.003 0.002 'International Tables'
H 0 64 0.000 0.000 'International Tables'
N 0 12 0.006 0.003 'International Tables'
O 0 4 0.011 0.006 'International Tables'
Cl 0 4 0.148 0.159 'International Tables'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1) N(1) C(10) 117.8(4) yes
C(1) N(2) C(2) 116.2(4) yes
C(1) N(2) C(11) 121.3(3) yes
C(2) N(2) C(11) 122.4(4) yes
C(2) N(3) C(3) 120.8(4) yes
C(12) N(4) C(21) 120.0(4) yes
C(12) N(5) C(13) 117.3(4) yes
C(12) N(5) C(22) 122.2(4) yes
C(13) N(5) C(22) 120.4(4) yes
C(13) N(6) C(14) 121.6(4) yes
O(1) C(1) N(1) 125.3(4) yes
O(1) C(1) N(2) 120.3(4) yes
N(1) C(1) N(2) 114.4(4) yes
N(2) C(2) N(3) 124.2(4) yes
N(3) C(3) C(4) 111.6(3) yes
C(3) C(4) C(5) 120.6(4) yes
C(3) C(4) C(9) 119.4(4) yes
C(5) C(4) C(9) 120.0(4) yes
C(4) C(5) C(6) 119.4(5) yes
C(5) C(6) C(7) 120.1(5) yes
C(6) C(7) C(8) 120.8(5) yes
C(7) C(8) C(9) 120.2(5) yes
C(4) C(9) C(8) 119.5(5) yes
O(2) C(12) N(4) 125.4(4) yes
O(2) C(12) N(5) 119.4(4) yes
N(4) C(12) N(5) 115.2(4) yes
N(5) C(13) N(6) 124.4(4) yes
N(6) C(14) C(15) 111.1(3) yes
C(14) C(15) C(16) 122.1(4) yes
C(14) C(15) C(20) 119.7(4) yes
C(16) C(15) C(20) 118.1(4) yes
C(15) C(16) C(17) 121.2(4) yes
C(16) C(17) C(18) 120.2(4) yes
C(17) C(18) C(19) 119.0(4) yes
C(18) C(19) C(20) 121.0(5) yes
C(15) C(20) C(19) 120.4(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) 1.217(5) yes
O(2) C(12) 1.222(5) yes
N(1) C(1) 1.334(6) yes
N(1) C(10) 1.470(6) yes
N(2) C(1) 1.441(5) yes
N(2) C(2) 1.348(5) yes
N(2) C(11) 1.461(5) yes
N(3) C(2) 1.297(5) yes
N(3) C(3) 1.477(5) yes
N(4) C(12) 1.330(6) yes
N(4) C(21) 1.452(6) yes
N(5) C(12) 1.446(5) yes
N(5) C(13) 1.340(6) yes
N(5) C(22) 1.465(6) yes
N(6) C(13) 1.289(5) yes
N(6) C(14) 1.482(6) yes
C(3) C(4) 1.517(6) yes
C(4) C(5) 1.382(6) yes
C(4) C(9) 1.395(6) yes
C(5) C(6) 1.407(7) yes
C(6) C(7) 1.368(8) yes
C(7) C(8) 1.369(8) yes
C(8) C(9) 1.394(7) yes
C(14) C(15) 1.509(6) yes
C(15) C(16) 1.396(6) yes
C(15) C(20) 1.402(6) yes
C(16) C(17) 1.384(6) yes
C(17) C(18) 1.387(7) yes
C(18) C(19) 1.390(7) yes
C(19) C(20) 1.378(7) yes
