#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:32:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178395 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/17/4021717.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_4021717
loop_
_publ_author_name
'Ying Cheng'
'Bo Wang'
'Lan-Qing Cheng'
_publ_section_title
;
 High Nucleophilicity of Cyclic Amidocarbene toward Aryl Isocyanates,
 New Approach to Spiro[azetidinone-4,3'-indolinone] Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4418
_journal_page_last               4427
_journal_paper_doi               10.1021/jo060265h
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C30 H27 Br2 N3 O3'
_chemical_formula_weight         637.37
_chemical_name_systematic
; 
 ? 
;
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.23(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.156(2)
_cell_length_b                   13.886(3)
_cell_length_c                   17.364(4)
_cell_measurement_reflns_used    25858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.86
_cell_volume                     2853.3(10)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Raxis Rapid IP'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_sigmaI/netI    0.1034
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25858
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    2.876
_exptl_absorpt_correction_T_max  0.5754
_exptl_absorpt_correction_T_min  0.2561
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   abscor
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         6526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.833
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.0526
_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)+(0.0679P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1471
_reflns_number_gt                2643
_reflns_number_total             6526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060265hsi20060208_085527.cif
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4021717
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Br1 Br 0.78979(5) 0.89311(5) 0.09438(3) 0.1003(3) Uani 1 1 d .
Br2 Br 0.53101(6) 1.05899(5) -0.08178(4) 0.1186(3) Uani 1 1 d .
O1 O 1.2432(2) 0.8138(2) -0.10410(17) 0.0775(9) Uani 1 1 d .
O2 O 0.9930(2) 0.97410(17) -0.26685(13) 0.0471(6) Uani 1 1 d .
O3 O 0.9222(3) 1.2955(2) -0.27888(19) 0.0990(12) Uani 1 1 d .
N1 N 1.0596(3) 0.8719(2) -0.15672(17) 0.0549(9) Uani 1 1 d .
N2 N 0.8867(3) 0.9149(2) -0.38586(17) 0.0493(8) Uani 1 1 d .
N3 N 0.8395(2) 1.14393(19) -0.30214(15) 0.0418(7) Uani 1 1 d .
C1 C 0.8810(3) 0.8853(3) -0.1197(2) 0.0566(11) Uani 1 1 d .
H1A H 0.8440 0.8877 -0.1728 0.068 Uiso 1 1 calc R
C2 C 0.8196(4) 0.8908(3) -0.0618(2) 0.0604(11) Uani 1 1 d .
H2B H 0.7415 0.8980 -0.0758 0.073 Uiso 1 1 calc R
C3 C 0.8748(4) 0.8854(3) 0.0156(2) 0.0607(11) Uani 1 1 d .
C4 C 0.9896(4) 0.8770(3) 0.0380(2) 0.0614(11) Uani 1 1 d .
H4A H 1.0256 0.8741 0.0914 0.074 Uiso 1 1 calc R
C5 C 1.0515(3) 0.8727(3) -0.0188(2) 0.0567(11) Uani 1 1 d .
H5A H 1.1297 0.8672 -0.0042 0.068 Uiso 1 1 calc R
C6 C 0.9962(3) 0.8765(3) -0.0986(2) 0.0495(10) Uani 1 1 d .
C7 C 1.1665(4) 0.8384(3) -0.1569(2) 0.0589(11) Uani 1 1 d .
C8 C 1.1427(4) 0.8418(3) -0.2477(2) 0.0696(13) Uani 1 1 d .
C9 C 1.0221(3) 0.8769(3) -0.2425(2) 0.0549(10) Uani 1 1 d .
H9A H 0.9624 0.8305 -0.2643 0.066 Uiso 1 1 calc R
C10 C 0.9199(3) 0.9835(3) -0.33765(19) 0.0392(8) Uani 1 1 d .
C11 C 0.7987(3) 0.9557(3) -0.44677(19) 0.0458(9) Uani 1 1 d .
C12 C 0.7319(4) 0.9077(3) -0.5096(2) 0.0653(12) Uani 1 1 d .
H12A H 0.7445 0.8432 -0.5192 0.078 Uiso 1 1 calc R
C13 C 0.6452(4) 0.9588(4) -0.5581(2) 0.0723(14) Uani 1 1 d .
H13A H 0.6006 0.9279 -0.6017 0.087 Uiso 1 1 calc R
C14 C 0.6221(4) 1.0541(3) -0.5443(2) 0.0618(12) Uani 1 1 d .
C15 C 0.6930(3) 1.1013(3) -0.4808(2) 0.0511(10) Uani 1 1 d .
H15A H 0.6806 1.1657 -0.4707 0.061 Uiso 1 1 calc R
C16 C 0.7809(3) 1.0523(3) -0.43360(19) 0.0422(9) Uani 1 1 d .
C17 C 0.8708(3) 1.0822(2) -0.36242(19) 0.0402(9) Uani 1 1 d .
C18 C 0.9567(3) 1.1666(3) -0.3731(2) 0.0532(10) Uani 1 1 d .
C19 C 0.9079(4) 1.2185(3) -0.3109(2) 0.0595(11) Uani 1 1 d .
C20 C 0.7644(3) 1.1268(3) -0.2533(2) 0.0458(9) Uani 1 1 d .
C21 C 0.7539(4) 1.1926(3) -0.1939(2) 0.0618(11) Uani 1 1 d .
H21A H 0.7944 1.2501 -0.1883 0.074 Uiso 1 1 calc R
C22 C 0.6845(4) 1.1724(4) -0.1445(2) 0.0725(14) Uani 1 1 d .
H22A H 0.6783 1.2159 -0.1051 0.087 Uiso 1 1 calc R
C23 C 0.6242(4) 1.0890(4) -0.1525(2) 0.0667(12) Uani 1 1 d .
C24 C 0.6300(3) 1.0253(3) -0.2112(2) 0.0574(11) Uani 1 1 d .
H24A H 0.5865 0.9695 -0.2175 0.069 Uiso 1 1 calc R
C25 C 0.7008(3) 1.0441(3) -0.2612(2) 0.0502(10) Uani 1 1 d .
H25A H 0.7056 1.0002 -0.3008 0.060 Uiso 1 1 calc R
C26 C 1.1388(5) 0.7399(4) -0.2836(3) 0.124(2) Uani 1 1 d .
H26A H 1.2138 0.7204 -0.2859 0.185 Uiso 1 1 calc R
H26B H 1.0913 0.7403 -0.3360 0.185 Uiso 1 1 calc R
H26C H 1.1089 0.6955 -0.2513 0.185 Uiso 1 1 calc R
C27 C 1.2156(4) 0.9107(4) -0.2800(3) 0.1045(19) Uani 1 1 d .
H27A H 1.2869 0.8808 -0.2797 0.157 Uiso 1 1 calc R
H27B H 1.2279 0.9676 -0.2477 0.157 Uiso 1 1 calc R
H27C H 1.1788 0.9278 -0.3332 0.157 Uiso 1 1 calc R
C28 C 0.5250(4) 1.1073(4) -0.5970(3) 0.0904(17) Uani 1 1 d .
H28A H 0.4855 1.0647 -0.6375 0.136 Uiso 1 1 calc R
H28B H 0.5537 1.1612 -0.6210 0.136 Uiso 1 1 calc R
H28C H 0.4743 1.1298 -0.5660 0.136 Uiso 1 1 calc R
C29 C 0.9358(4) 1.2140(3) -0.4535(2) 0.0762(14) Uani 1 1 d .
H29A H 0.9915 1.2631 -0.4531 0.114 Uiso 1 1 calc R
H29B H 0.8618 1.2424 -0.4656 0.114 Uiso 1 1 calc R
H29C H 0.9407 1.1666 -0.4928 0.114 Uiso 1 1 calc R
C30 C 1.0806(3) 1.1428(4) -0.3439(3) 0.0854(16) Uani 1 1 d .
H30A H 1.1254 1.1970 -0.3523 0.128 Uiso 1 1 calc R
H30B H 1.0991 1.0881 -0.3723 0.128 Uiso 1 1 calc R
H30C H 1.0960 1.1281 -0.2884 0.128 Uiso 1 1 calc R
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'
Br Br -0.2901 2.4595 '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
C10 O2 C9 115.3(3)
C7 N1 C6 133.5(3)
C7 N1 C9 95.0(3)
C6 N1 C9 129.6(3)
C10 N2 C11 105.0(3)
C19 N3 C20 134.2(3)
C19 N3 C17 95.8(3)
C20 N3 C17 130.0(3)
C6 C1 C2 120.0(4)
C3 C2 C1 119.3(4)
C2 C3 C4 121.8(4)
C2 C3 Br1 118.9(3)
C4 C3 Br1 119.3(3)
C3 C4 C5 119.4(4)
C4 C5 C6 119.6(4)
C1 C6 C5 119.9(4)
C1 C6 N1 120.5(3)
C5 C6 N1 119.5(4)
O1 C7 N1 131.4(4)
O1 C7 C8 136.5(4)
N1 C7 C8 92.0(3)
C27 C8 C7 114.5(4)
C27 C8 C26 113.6(4)
C7 C8 C26 111.6(4)
C27 C8 C9 117.6(4)
C7 C8 C9 84.9(3)
C26 C8 C9 111.5(4)
O2 C9 N1 110.2(3)
O2 C9 C8 116.6(3)
N1 C9 C8 88.0(3)
N2 C10 O2 124.8(3)
N2 C10 C17 116.5(3)
O2 C10 C17 118.7(3)
C12 C11 C16 120.9(4)
C12 C11 N2 126.8(3)
C16 C11 N2 112.2(3)
C11 C12 C13 117.6(4)
C12 C13 C14 122.8(4)
C13 C14 C15 118.1(4)
C13 C14 C28 121.6(4)
C15 C14 C28 120.2(4)
C16 C15 C14 119.7(4)
C15 C16 C11 120.8(3)
C15 C16 C17 132.3(3)
C11 C16 C17 106.9(3)
N3 C17 C16 119.1(3)
N3 C17 C10 118.3(3)
C16 C17 C10 98.5(3)
N3 C17 C18 86.4(3)
C16 C17 C18 118.3(3)
C10 C17 C18 117.9(3)
C30 C18 C29 110.4(4)
C30 C18 C19 112.6(3)
C29 C18 C19 116.0(4)
C30 C18 C17 115.1(3)
C29 C18 C17 116.6(3)
C19 C18 C17 84.0(3)
O3 C19 N3 131.0(4)
O3 C19 C18 135.2(4)
N3 C19 C18 93.8(3)
C25 C20 N3 120.7(3)
C25 C20 C21 118.3(4)
N3 C20 C21 121.0(4)
C22 C21 C20 120.0(4)
C21 C22 C23 120.6(4)
C22 C23 C24 120.6(4)
C22 C23 Br2 120.6(3)
C24 C23 Br2 118.8(4)
C23 C24 C25 119.6(4)
C20 C25 C24 120.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.896(4)
Br2 C23 1.897(4)
O1 C7 1.198(4)
O2 C10 1.349(4)
O2 C9 1.434(4)
O3 C19 1.199(5)
N1 C7 1.381(5)
N1 C6 1.405(5)
N1 C9 1.457(5)
N2 C10 1.271(4)
N2 C11 1.438(4)
N3 C19 1.357(5)
N3 C20 1.402(4)
N3 C17 1.469(4)
C1 C6 1.369(5)
C1 C2 1.384(5)
C2 C3 1.361(5)
C3 C4 1.366(6)
C4 C5 1.372(5)
C5 C6 1.396(5)
C7 C8 1.536(5)
C8 C27 1.498(6)
C8 C26 1.543(7)
C8 C9 1.566(6)
C10 C17 1.517(5)
C11 C12 1.374(5)
C11 C16 1.387(5)
C12 C13 1.385(6)
C13 C14 1.384(6)
C14 C15 1.399(5)
C14 C28 1.510(6)
C15 C16 1.369(5)
C16 C17 1.509(5)
C17 C18 1.608(5)
C18 C30 1.512(5)
C18 C29 1.511(5)
C18 C19 1.526(6)
C20 C25 1.373(5)
C20 C21 1.406(5)
C21 C22 1.362(6)
C22 C23 1.360(6)
C23 C24 1.364(6)
C24 C25 1.380(5)
