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_1512044
_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         'C30 H33 Au N3 O P'
_chemical_formula_sum            'C30 H33 Au N3 O P'
_chemical_formula_weight         679.55
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             11-07-19
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2011-07-20 - Report on C30 H33 Au N3 O P
             by Anthony C. Willis
             for   Pat Sharp and Martin Banwell

2011-07-20 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1923(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3557(1)
_cell_length_b                   15.3193(2)
_cell_length_c                   14.7851(2)
_cell_measurement_reflns_used    46010
_cell_measurement_temperature    200
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2.6
_cell_volume                     2889.87(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.042
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            82634
_diffrn_reflns_theta_full        30.032
_diffrn_reflns_theta_max         30.032
_diffrn_reflns_theta_min         2.659
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.172
_exptl_absorpt_correction_T_max  0.66
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.98
_refine_diff_density_min         -1.10
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9879
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         8436
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.0242070
_refine_ls_shift/su_mean         0.0008453
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 2.98P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0548
_refine_ls_wR_factor_gt          0.0500
_refine_ls_wR_factor_ref         0.0548
_reflns_limit_h_max              17
_reflns_limit_h_min              -18
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                6955
_reflns_number_total             8437
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.40
_oxford_diffrn_Wilson_scale      23.85
_oxford_refine_ls_r_factor_ref   0.0361
_oxford_refine_ls_scale          0.17282(4)
_oxford_reflns_number_all        8436
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '7181750 ban1121 scalepacked'
_cod_data_source_file            ol4007986_si_010.cif
_cod_data_source_block           ban1121
_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/n 1 '
_cod_database_code               1512044
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT H(331,X'S) H(351,X'S) H(352,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) H   ( 153,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) H   ( 163,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) H   ( 193,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;