Consecutive Gold(I)-Catalyzed Cyclization Reactions of o-(Buta-1,3-diyn-1-yl-)-Substituted N-Aryl Ureas: A One-Pot Synthesis of Pyrimido[1,6-a]indol-1(2H)-ones and Related Systems.
Sharp, Phillip P.; Banwell, Martin G.; Renner, Jens; Lohmann, Klaas; Willis, Anthony C.; Organic letters 15 (2013) 2616–2619; doi:10.1021/ol4007986

data_1512039
_publ_section_title
;
 Consecutive Gold(I)-Catalyzed Cyclization Reactions of
 o-(Buta-1,3-diyn-1-yl-)-Substituted N-Aryl Ureas: A One-Pot Synthesis of
 Pyrimido[1,6-a]indol-1(2H)-ones and Related Systems.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2616
_journal_page_last               2619
_journal_paper_doi               10.1021/ol4007986
_journal_volume                  15
_journal_year                    2013
_chemical_compound_source        local
_chemical_formula_moiety         'C16 H15 Cl3 N2 O2 Si'
_chemical_formula_sum            'C16 H15 Cl3 N2 O2 Si'
_chemical_formula_weight         401.75
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_audit_creation_date             11-07-04
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2011-07-05 - Report on C16 H15 Cl3 N2 O2 Si
             by Anthony C. Willis
             for   Pat Sharp and Martin Banwell

2011-06-03 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 91.5937(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1127(2)
_cell_length_b                   11.3456(5)
_cell_length_c                   28.0659(11)
_cell_measurement_reflns_used    76447
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.6
_cell_volume                     1945.68(13)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997),
;
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.101
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23034
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         2.823
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0235
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3425
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0696
_refine_ls_shift/su_max          0.0123914
_refine_ls_shift/su_mean         0.0006013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.11P)^2^ + 5.36P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2091
_refine_ls_wR_factor_gt          0.1898
_refine_ls_wR_factor_ref         0.2091
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              33
_reflns_limit_l_min              0
_reflns_number_gt                2749
_reflns_number_total             3428
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.01
_oxford_diffrn_Wilson_scale      5.65
_oxford_refine_ls_r_factor_ref   0.0884
_oxford_refine_ls_scale          0.4943(19)
_oxford_reflns_number_all        3425
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '7041609 ban1106B twinning'
_cod_data_source_file            ol4007986_si_004.cif
_cod_data_source_block           ban1106B
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               1512039
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT H(151,X'S) H(181,X'S) 
SUMFIX ELEMENT SCALES 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 0.87, .03 = N(15) TO H(151) 
DIST 0.87, .03 = N(18) TO H(181) 
ANGLE 0.0, 3. = MEAN C(1) TO N(15) TO H(151) 
CONT                 C(16) TO N(15) TO H(151) 
ANGLE 0.0, 3. = MEAN C(16) TO N(18) TO H(181) 
CONT                 C(19) TO N(18) TO H(181) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;