#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:03:08 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178592 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/03/4070315.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_4070315
loop_
_publ_author_name
'Welch, Kevin D.'
'Harrison, Daniel P.'
'Sabat, Michal'
'Hejazi, Emily Z.'
'Parr, Brendan T.'
'Fanelli, Matthew G.'
'Gianfrancesco, Nicole A.'
'Nagra, Dalsher S.'
'Myers, William H.'
'Harman, W. Dean'
_publ_section_title
;
 Michael−Aldol Ring Closures with Dihapto-Coordinated Pyrrole
 Complexes and the Synthesis of Tetrahydroindole Cores
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              5960
_journal_paper_doi               10.1021/om900714r
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C24 H36 B N8 O3 P W'
_chemical_formula_weight         710.24
_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                 90.92(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.060(2)
_cell_length_b                   11.610(2)
_cell_length_c                   22.088(4)
_cell_measurement_reflns_used    7905
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      17.421
_cell_measurement_theta_min      2.698
_cell_volume                     2835.9(9)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      153(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'omega and phi 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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            25995
_diffrn_reflns_theta_full        36.43
_diffrn_reflns_theta_max         36.43
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    4.171
_exptl_absorpt_correction_T_max  0.89743
_exptl_absorpt_correction_T_min  0.56871
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1416
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.713
_refine_diff_density_min         -1.539
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         13485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0256
_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)+(0.0338P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0641
_reflns_number_gt                11434
_reflns_number_total             13485
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om900714r_si_001.cif
_cod_data_source_block           C22H33BN8O2PW-acetone
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2835.9(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4070315
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
W W 0.484375(5) 0.184048(5) 0.178943(3) 0.01523(2) Uani 1 1 d
P P 0.67413(4) 0.09766(4) 0.22195(2) 0.01830(8) Uani 1 1 d
O1 O 0.69646(13) 0.49299(14) -0.03485(6) 0.0259(3) Uani 1 1 d
O2 O 0.55368(12) 0.42559(12) 0.21353(7) 0.0253(3) Uani 1 1 d
O3 O 0.1087(10) 0.9848(10) 0.0416(6) 0.329(8) Uani 1 1 d
N1 N 0.48178(14) 0.34706(15) 0.06738(7) 0.0202(3) Uani 1 1 d
N2 N 0.28570(14) 0.20050(14) 0.16971(8) 0.0215(3) Uani 1 1 d
N3 N 0.21230(14) 0.12387(15) 0.19886(9) 0.0288(4) Uani 1 1 d
N4 N 0.43499(13) -0.00187(14) 0.16456(8) 0.0224(3) Uani 1 1 d
N5 N 0.34635(15) -0.04946(15) 0.19875(9) 0.0283(3) Uani 1 1 d
N6 N 0.42644(15) 0.16072(15) 0.27304(7) 0.0226(3) Uani 1 1 d
N7 N 0.34073(16) 0.08375(15) 0.28926(9) 0.0286(4) Uani 1 1 d
N8 N 0.52413(13) 0.32745(12) 0.19870(7) 0.0171(2) Uani 1 1 d
C2 C 0.47893(16) 0.22279(17) 0.08059(8) 0.0200(3) Uani 1 1 d
C3 C 0.60052(16) 0.18526(16) 0.09729(8) 0.0197(3) Uani 1 1 d
C4 C 0.68210(16) 0.29044(17) 0.09154(8) 0.0201(3) Uani 1 1 d
C5 C 0.59019(15) 0.38262(16) 0.07603(7) 0.0186(3) Uani 1 1 d
C6 C 0.63409(16) 0.50406(17) 0.06960(8) 0.0207(3) Uani 1 1 d
C7 C 0.74151(16) 0.50935(17) 0.02565(8) 0.0219(3) Uani 1 1 d
C8 C 0.83254(17) 0.41204(19) 0.03774(9) 0.0247(4) Uani 1 1 d
C9 C 0.77506(18) 0.29159(19) 0.04050(9) 0.0244(3) Uani 1 1 d
C10 C 0.80493(19) 0.62559(19) 0.03163(10) 0.0288(4) Uani 1 1 d
C11 C 0.3983(2) 0.1543(2) 0.03829(9) 0.0278(4) Uani 1 1 d
C12 C 0.09588(19) 0.1528(2) 0.18855(14) 0.0378(5) Uani 1 1 d
C13 C 0.09209(19) 0.2493(2) 0.15232(12) 0.0359(5) Uani 1 1 d
C14 C 0.21308(18) 0.27597(18) 0.14157(10) 0.0256(4) Uani 1 1 d
C15 C 0.3380(2) -0.1627(2) 0.18744(13) 0.0358(5) Uani 1 1 d
C16 C 0.4233(2) -0.19164(19) 0.14509(14) 0.0359(5) Uani 1 1 d
C17 C 0.48147(18) -0.08877(18) 0.13236(10) 0.0275(4) Uani 1 1 d
C18 C 0.3256(2) 0.0908(2) 0.35028(11) 0.0387(6) Uani 1 1 d
C19 C 0.4027(3) 0.1719(2) 0.37334(11) 0.0376(6) Uani 1 1 d
C20 C 0.4635(2) 0.2150(2) 0.32379(9) 0.0288(4) Uani 1 1 d
C22 C 0.64285(17) -0.01194(18) 0.27862(9) 0.0246(3) Uani 1 1 d
C23 C 0.7771(2) 0.19243(19) 0.26284(12) 0.0308(4) Uani 1 1 d
C24 C 0.77875(18) 0.0223(2) 0.17272(10) 0.0272(4) Uani 1 1 d
C25 C 0.0014(13) 0.9608(9) 0.0297(4) 0.161(4) Uani 1 1 d
C26 C -0.0783(7) 0.8979(7) 0.0640(4) 0.145(3) Uani 1 1 d
B1 B 0.2647(2) 0.0259(2) 0.23926(13) 0.0307(5) Uani 1 1 d
H1B H 0.197(2) -0.022(2) 0.2557(12) 0.029(7) Uiso 1 1 d
H1O H 0.643(3) 0.549(3) -0.0449(15) 0.052(9) Uiso 1 1 d
H3 H 0.626(3) 0.113(3) 0.0802(13) 0.032(7) Uiso 1 1 d
H4 H 0.724(2) 0.3079(19) 0.1258(12) 0.017(6) Uiso 1 1 d
H6A H 0.570(2) 0.556(2) 0.0562(11) 0.020(6) Uiso 1 1 d
H6B H 0.655(2) 0.534(2) 0.1079(12) 0.026(6) Uiso 1 1 d
H8A H 0.876(2) 0.432(2) 0.0751(11) 0.017(5) Uiso 1 1 d
H8B H 0.890(2) 0.417(2) 0.0078(12) 0.025(6) Uiso 1 1 d
H9A H 0.836(2) 0.230(2) 0.0472(11) 0.021(6) Uiso 1 1 d
H9B H 0.735(2) 0.274(2) 0.0023(12) 0.025(6) Uiso 1 1 d
H10A H 0.868(3) 0.632(3) -0.0025(14) 0.041(8) Uiso 1 1 d
H10B H 0.840(2) 0.632(2) 0.0726(12) 0.031(7) Uiso 1 1 d
H10C H 0.754(3) 0.697(3) 0.0277(15) 0.041(9) Uiso 1 1 d
H11A H 0.416(3) 0.167(2) -0.0049(14) 0.030(7) Uiso 1 1 d
H11B H 0.414(3) 0.076(3) 0.0462(13) 0.039(8) Uiso 1 1 d
H11C H 0.313(3) 0.168(2) 0.0443(14) 0.037(8) Uiso 1 1 d
H12 H 0.037(3) 0.110(3) 0.2073(14) 0.048(9) Uiso 1 1 d
H13 H 0.023(3) 0.289(3) 0.1352(15) 0.050(9) Uiso 1 1 d
H14 H 0.247(2) 0.333(2) 0.1222(12) 0.022(6) Uiso 1 1 d
H15 H 0.279(3) -0.212(3) 0.2087(14) 0.039(8) Uiso 1 1 d
H16 H 0.437(3) -0.254(3) 0.1255(13) 0.038(8) Uiso 1 1 d
H17 H 0.544(2) -0.078(2) 0.1072(11) 0.019(5) Uiso 1 1 d
H18 H 0.266(3) 0.044(3) 0.3605(16) 0.054(10) Uiso 1 1 d
H19 H 0.416(4) 0.191(3) 0.422(2) 0.090(16) Uiso 1 1 d
H20 H 0.523(2) 0.276(3) 0.3190(12) 0.040(9) Uiso 1 1 d
H22A H 0.589(3) -0.064(2) 0.2619(13) 0.034(7) Uiso 1 1 d
H22B H 0.603(2) 0.029(2) 0.3130(12) 0.028(6) Uiso 1 1 d
H22C H 0.722(2) -0.043(2) 0.2930(11) 0.024(6) Uiso 1 1 d
H23A H 0.841(2) 0.145(2) 0.2817(12) 0.028(6) Uiso 1 1 d
H23B H 0.730(3) 0.239(3) 0.2893(14) 0.044(8) Uiso 1 1 d
H23C H 0.813(3) 0.239(3) 0.2355(15) 0.047(9) Uiso 1 1 d
H24A H 0.742(3) -0.040(3) 0.1496(17) 0.063(10) Uiso 1 1 d
H24B H 0.816(3) 0.070(3) 0.1441(14) 0.042(8) Uiso 1 1 d
H24C H 0.847(2) -0.017(2) 0.1961(12) 0.029(7) Uiso 1 1 d
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'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -0.8490 6.8722 '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
_geom_angle_site_symmetry_3
N8 W N6 87.59(7) .
N8 W N2 100.57(6) .
N6 W N2 78.11(7) .
N8 W C2 93.06(7) .
N6 W C2 161.04(6) .
N2 W C2 83.16(7) .
N8 W C3 92.83(7) .
N6 W C3 160.75(7) .
N2 W C3 120.59(7) .
C2 W C3 38.19(7) .
N8 W N4 173.87(6) .
N6 W N4 86.65(6) .
N2 W N4 80.28(6) .
C2 W N4 93.07(7) .
C3 W N4 91.92(6) .
N8 W P 94.58(5) .
N6 W P 81.21(5) .
N2 W P 153.70(5) .
C2 W P 117.58(5) .
C3 W P 79.57(5) .
N4 W P 82.47(4) .
C23 P C22 101.90(11) .
C23 P C24 100.89(11) .
C22 P C24 101.75(10) .
C23 P W 117.53(8) .
C22 P W 111.95(7) .
C24 P W 120.17(7) .
C5 N1 C2 108.03(15) .
C14 N2 N3 106.74(16) .
C14 N2 W 133.54(14) .
N3 N2 W 119.68(12) .
C12 N3 N2 109.28(19) .
C12 N3 B1 128.86(19) .
N2 N3 B1 121.78(15) .
C17 N4 N5 105.89(16) .
C17 N4 W 134.65(13) .
N5 N4 W 119.06(12) .
C15 N5 N4 109.97(18) .
C15 N5 B1 128.42(18) .
N4 N5 B1 121.40(16) .
C20 N6 N7 107.09(17) .
C20 N6 W 129.81(14) .
N7 N6 W 123.10(14) .
N6 N7 C18 108.6(2) .
N6 N7 B1 118.46(17) .
C18 N7 B1 131.7(2) .
O2 N8 W 178.31(14) .
C3 C2 N1 108.72(15) .
C3 C2 C11 122.27(17) .
N1 C2 C11 114.10(16) .
C3 C2 W 71.38(10) .
N1 C2 W 113.11(11) .
C11 C2 W 120.42(14) .
C2 C3 C4 106.54(15) .
C2 C3 W 70.44(10) .
C4 C3 W 114.94(12) .
C5 C4 C3 100.90(14) .
C5 C4 C9 106.43(15) .
C3 C4 C9 118.13(16) .
N1 C5 C6 126.41(16) .
N1 C5 C4 115.50(17) .
C6 C5 C4 118.03(15) .
C5 C6 C7 110.49(15) .
O1 C7 C10 110.54(16) .
O1 C7 C8 106.41(16) .
C10 C7 C8 109.69(16) .
O1 C7 C6 108.73(14) .
C10 C7 C6 109.71(17) .
C8 C7 C6 111.71(15) .
C7 C8 C9 113.96(16) .
C8 C9 C4 108.58(17) .
N3 C12 C13 108.7(2) .
C12 C13 C14 104.98(19) .
N2 C14 C13 110.3(2) .
N5 C15 C16 108.6(2) .
C15 C16 C17 104.6(2) .
N4 C17 C16 110.9(2) .
N7 C18 C19 109.0(2) .
C18 C19 C20 105.2(2) .
N6 C20 C19 110.1(2) .
O3 C25 C26 128.1(12) .
O3 C25 C25 93.0(15) 3_575
C26 C25 C25 138.5(16) 3_575
N7 B1 N5 110.21(17) .
N7 B1 N3 106.77(17) .
N5 B1 N3 107.29(19) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
W N8 1.7747(15) .
W N6 2.2015(16) .
W N2 2.2118(16) .
W C2 2.2184(18) .
W C3 2.2310(18) .
W N4 2.2479(17) .
W P 2.4998(7) .
P C23 1.814(2) .
P C22 1.822(2) .
P C24 1.824(2) .
O1 C7 1.431(2) .
O2 N8 1.228(2) .
O3 C25 1.243(14) .
N1 C5 1.280(2) .
N1 C2 1.472(2) .
N2 C14 1.335(3) .
N2 N3 1.372(2) .
N3 C12 1.347(3) .
N3 B1 1.552(3) .
N4 C17 1.341(3) .
N4 N5 1.364(2) .
N5 C15 1.342(3) .
N5 B1 1.551(3) .
N6 C20 1.344(3) .
N6 N7 1.355(2) .
N7 C18 1.363(3) .
N7 B1 1.532(4) .
C2 C3 1.455(3) .
C2 C11 1.508(3) .
C3 C4 1.525(3) .
C4 C5 1.512(3) .
C4 C9 1.538(3) .
C5 C6 1.499(3) .
C6 C7 1.547(2) .
C7 C10 1.526(3) .
C7 C8 1.534(3) .
C8 C9 1.538(3) .
C12 C13 1.377(4) .
C13 C14 1.397(3) .
C15 C16 1.380(4) .
C16 C17 1.388(3) .
C18 C19 1.363(4) .
C19 C20 1.387(3) .
C25 C26 1.381(13) .
C25 C25 1.60(2) 3_575
