#------------------------------------------------------------------------------
#$Date: 2019-06-25 10:01:44 +0300 (Tue, 25 Jun 2019) $
#$Revision: 216516 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/18/1551875.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_1551875
loop_
_publ_author_name
'Stefan Michlik'
'Rhett Kempe'
_publ_section_title
;
 A sustainable catalytic pyrrole synthesis
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              140
_journal_page_last               144
_journal_paper_doi               10.1038/nchem.1547
_journal_volume                  5
_journal_year                    2013
_chemical_formula_sum            'C29 H46 Ir N5 P2'
_chemical_formula_weight         718.85
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   19.8530(11)
_cell_length_b                   42.232(2)
_cell_length_c                   14.7820(12)
_cell_measurement_reflns_used    22085
_cell_measurement_temperature    133(2)
_cell_volume                     12393.7(14)
_computing_cell_refinement       X-AREA-STOE
_computing_data_collection       X-AREA-STOE
_computing_data_reduction        X-RED32
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  STOE-IPDSII
_diffrn_measurement_method       Omega-Scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1141
_diffrn_reflns_av_sigmaI/netI    0.0946
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19287
_diffrn_reflns_theta_full        24.73
_diffrn_reflns_theta_max         24.73
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    4.438
_exptl_absorpt_correction_T_max  0.2351
_exptl_absorpt_correction_T_min  0.1283
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5792
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         2.759
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.177
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.014(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5231
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0641
_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)+(0.0846P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                3973
_reflns_number_total             5231
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            nchem.1547-s2.cif
_cod_data_source_block           t257ofma1
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               1551875
_cell_measurement_2theta_min     3.56
_cell_measurement_2theta_max     45.95
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.53224(3) 0.218670(14) 0.95948(4) 0.04982(18) Uani 1 1 d . . .
P1 P 0.6362(2) 0.19443(9) 0.9383(2) 0.0486(9) Uani 1 1 d . . .
P2 P 0.45130(18) 0.25714(9) 0.9615(4) 0.0572(10) Uani 1 1 d . . .
N1 N 0.5797(6) 0.3074(3) 0.8350(9) 0.050(3) Uani 1 1 d . . .
N2 N 0.6776(6) 0.2748(3) 0.8203(8) 0.045(3) Uani 1 1 d . . .
N3 N 0.5774(6) 0.2527(4) 0.8955(8) 0.062(4) Uani 1 1 d . . .
N4 N 0.6755(6) 0.2242(3) 0.8796(8) 0.049(3) Uani 1 1 d . . .
H1N H 0.7167 0.2210 0.8595 0.058 Uiso 1 1 calc R . .
N5 N 0.4842(7) 0.2877(3) 0.9047(10) 0.064(4) Uani 1 1 d . . .
C1 C 0.4587(9) 0.1830(4) 0.9842(11) 0.060(3) Uani 1 1 d . . .
H1 H 0.4118 0.1916 0.9846 0.072 Uiso 1 1 calc R . .
C2 C 0.4931(9) 0.1892(4) 1.0643(12) 0.060(3) Uani 1 1 d . . .
H2 H 0.4648 0.2015 1.1077 0.072 Uiso 1 1 calc R . .
C3 C 0.5354(9) 0.1651(4) 1.1118(12) 0.066(3) Uani 1 1 d . . .
H3A H 0.5653 0.1761 1.1551 0.079 Uiso 1 1 calc R . .
H3B H 0.5643 0.1544 1.0667 0.079 Uiso 1 1 calc R . .
C4 C 0.4951(11) 0.1399(4) 1.1631(13) 0.077(4) Uani 1 1 d D . .
H4A H 0.5157 0.1367 1.2234 0.092 Uiso 1 1 calc R . .
H4B H 0.4486 0.1477 1.1725 0.092 Uiso 1 1 calc R . .
C5 C 0.4924(18) 0.1082(5) 1.1134(17) 0.141(9) Uani 1 1 d D . .
H5 H 0.5150 0.0906 1.1391 0.169 Uiso 1 1 calc R . .
C6 C 0.4574(15) 0.1041(6) 1.0302(18) 0.141(9) Uani 1 1 d D . .
H6 H 0.4614 0.0836 1.0043 0.169 Uiso 1 1 calc R . .
C7 C 0.4148(10) 0.1272(4) 0.9763(13) 0.077(4) Uani 1 1 d D . .
H7A H 0.3821 0.1380 1.0164 0.092 Uiso 1 1 calc R . .
H7B H 0.3895 0.1159 0.9284 0.092 Uiso 1 1 calc R . .
C8 C 0.4644(9) 0.1520(4) 0.9331(11) 0.066(3) Uani 1 1 d . . .
H8A H 0.5112 0.1440 0.9365 0.079 Uiso 1 1 calc R . .
H8B H 0.4529 0.1553 0.8686 0.079 Uiso 1 1 calc R . .
C9 C 0.5482(7) 0.2824(4) 0.8758(10) 0.050(4) Uani 1 1 d . . .
C10 C 0.6435(8) 0.3017(3) 0.8063(9) 0.048(4) Uani 1 1 d . . .
C11 C 0.6760(8) 0.3272(4) 0.7583(11) 0.054(4) Uani 1 1 d . . .
C12 C 0.6648(8) 0.3581(4) 0.7817(11) 0.054(4) Uani 1 1 d . . .
H12 H 0.6355 0.3630 0.8306 0.065 Uiso 1 1 calc R . .
C13 C 0.6959(8) 0.3823(4) 0.7347(11) 0.058(4) Uani 1 1 d . . .
H13 H 0.6885 0.4037 0.7523 0.070 Uiso 1 1 calc R . .
C14 C 0.7375(9) 0.3758(5) 0.6628(14) 0.071(5) Uani 1 1 d . . .
H14 H 0.7568 0.3927 0.6292 0.085 Uiso 1 1 calc R . .
C15 C 0.7516(8) 0.3441(4) 0.6384(11) 0.057(4) Uani 1 1 d . . .
H15 H 0.7812 0.3394 0.5896 0.068 Uiso 1 1 calc R . .
C16 C 0.7221(8) 0.3206(4) 0.6859(10) 0.056(4) Uani 1 1 d . . .
H16 H 0.7321 0.2992 0.6712 0.068 Uiso 1 1 calc R . .
C17 C 0.6463(7) 0.2517(3) 0.8634(9) 0.043(3) Uani 1 1 d . . .
C18 C 0.6799(10) 0.2193(4) 1.0952(14) 0.067(5) Uani 1 1 d . . .
H18A H 0.7043 0.2170 1.1524 0.101 Uiso 1 1 calc R . .
H18B H 0.6317 0.2217 1.1075 0.101 Uiso 1 1 calc R . .
H18C H 0.6964 0.2381 1.0632 0.101 Uiso 1 1 calc R . .
C19 C 0.7673(9) 0.1852(4) 1.0167(12) 0.066(5) Uani 1 1 d . . .
H19A H 0.7840 0.2024 0.9784 0.099 Uiso 1 1 calc R . .
H19B H 0.7730 0.1649 0.9851 0.099 Uiso 1 1 calc R . .
H19C H 0.7928 0.1848 1.0734 0.099 Uiso 1 1 calc R . .
C20 C 0.6117(9) 0.1606(5) 0.7832(13) 0.069(5) Uani 1 1 d . . .
H20A H 0.6190 0.1410 0.7490 0.104 Uiso 1 1 calc R . .
H20B H 0.6234 0.1788 0.7453 0.104 Uiso 1 1 calc R . .
H20C H 0.5643 0.1620 0.8011 0.104 Uiso 1 1 calc R . .
C21 C 0.3869(12) 0.2359(6) 0.8051(14) 0.093(7) Uani 1 1 d . . .
H21A H 0.3460 0.2272 0.7775 0.140 Uiso 1 1 calc R . .
H21B H 0.4202 0.2190 0.8125 0.140 Uiso 1 1 calc R . .
H21C H 0.4055 0.2525 0.7659 0.140 Uiso 1 1 calc R . .
C22 C 0.6525(9) 0.1278(4) 0.9120(12) 0.066(4) Uani 1 1 d . . .
H22A H 0.6069 0.1241 0.9351 0.098 Uiso 1 1 calc R . .
H22B H 0.6848 0.1268 0.9621 0.098 Uiso 1 1 calc R . .
H22C H 0.6637 0.1115 0.8672 0.098 Uiso 1 1 calc R . .
C23 C 0.3259(10) 0.2795(5) 0.8941(16) 0.090(7) Uani 1 1 d . . .
H23A H 0.2886 0.2757 0.8520 0.136 Uiso 1 1 calc R . .
H23B H 0.3529 0.2974 0.8725 0.136 Uiso 1 1 calc R . .
H23C H 0.3078 0.2844 0.9542 0.136 Uiso 1 1 calc R . .
C24 C 0.3734(11) 0.2565(5) 1.1188(14) 0.081(6) Uani 1 1 d . . .
H24A H 0.3878 0.2344 1.1247 0.122 Uiso 1 1 calc R . .
H24B H 0.3313 0.2574 1.0845 0.122 Uiso 1 1 calc R . .
H24C H 0.3664 0.2656 1.1790 0.122 Uiso 1 1 calc R . .
C25 C 0.4898(11) 0.2803(6) 1.1263(14) 0.087(6) Uani 1 1 d . . .
H25A H 0.5221 0.2936 1.0937 0.131 Uiso 1 1 calc R . .
H25B H 0.5106 0.2597 1.1393 0.131 Uiso 1 1 calc R . .
H25C H 0.4771 0.2906 1.1831 0.131 Uiso 1 1 calc R . .
C26 C 0.4280(9) 0.2754(5) 1.0689(12) 0.065(5) Uani 1 1 d . . .
H26 H 0.4090 0.2968 1.0551 0.078 Uiso 1 1 calc R . .
C27 C 0.6910(8) 0.1906(4) 1.0377(9) 0.047(3) Uani 1 1 d . . .
H27 H 0.6749 0.1718 1.0730 0.056 Uiso 1 1 calc R . .
C28 C 0.3694(9) 0.2503(5) 0.8997(12) 0.071(5) Uani 1 1 d . . .
H28 H 0.3436 0.2339 0.9341 0.086 Uiso 1 1 calc R . .
C29 C 0.6560(8) 0.1605(4) 0.8676(9) 0.049(4) Uani 1 1 d . . .
H29 H 0.7034 0.1634 0.8464 0.058 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 '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_1
_geom_angle_site_symmetry_3
N3 Ir1 C1 157.6(5) . .
N3 Ir1 C2 162.6(5) . .
C1 Ir1 C2 38.1(6) . .
N3 Ir1 P2 78.7(4) . .
C1 Ir1 P2 91.1(5) . .
C2 Ir1 P2 98.6(5) . .
N3 Ir1 P1 81.4(4) . .
C1 Ir1 P1 108.7(5) . .
C2 Ir1 P1 99.4(5) . .
P2 Ir1 P1 159.88(14) . .
N4 P1 C29 100.8(6) . .
N4 P1 C27 101.5(6) . .
C29 P1 C27 105.2(7) . .
N4 P1 Ir1 98.6(5) . .
C29 P1 Ir1 128.1(5) . .
C27 P1 Ir1 117.3(5) . .
N5 P2 C26 102.1(8) . .
N5 P2 C28 102.2(8) . .
C26 P2 C28 105.5(8) . .
N5 P2 Ir1 105.5(5) . .
C26 P2 Ir1 119.3(6) . .
C28 P2 Ir1 119.4(6) . .
C10 N1 C9 115.2(12) . .
C17 N2 C10 117.5(13) . .
C9 N3 C17 110.4(14) . .
C9 N3 Ir1 124.6(10) . .
C17 N3 Ir1 125.0(11) . .
C17 N4 P1 122.4(11) . .
C9 N5 P2 113.4(12) . .
C2 C1 C8 123.3(15) . .
C2 C1 Ir1 71.1(11) . .
C8 C1 Ir1 118.3(11) . .
C1 C2 C3 123.2(15) . .
C1 C2 Ir1 70.7(10) . .
C3 C2 Ir1 122.3(13) . .
C2 C3 C4 114.3(16) . .
C5 C4 C3 112.8(17) . .
C6 C5 C4 123(3) . .
C5 C6 C7 130(2) . .
C6 C7 C8 107.0(17) . .
C1 C8 C7 109.0(13) . .
N5 C9 N1 116.1(14) . .
N5 C9 N3 117.8(14) . .
N1 C9 N3 126.0(13) . .
N2 C10 N1 125.2(13) . .
N2 C10 C11 118.9(14) . .
N1 C10 C11 115.9(13) . .
C12 C11 C16 118.5(15) . .
C12 C11 C10 121.1(15) . .
C16 C11 C10 120.4(15) . .
C11 C12 C13 120.4(15) . .
C14 C13 C12 120.7(18) . .
C13 C14 C15 120.3(18) . .
C16 C15 C14 118.4(15) . .
C15 C16 C11 121.5(15) . .
N4 C17 N2 122.1(13) . .
N4 C17 N3 112.5(14) . .
N2 C17 N3 125.4(13) . .
C25 C26 C24 112.0(17) . .
C25 C26 P2 110.0(12) . .
C24 C26 P2 112.1(13) . .
C18 C27 C19 111.9(14) . .
C18 C27 P1 107.1(11) . .
C19 C27 P1 115.4(10) . .
C23 C28 C21 113.3(17) . .
C23 C28 P2 113.3(15) . .
C21 C28 P2 107.5(13) . .
C20 C29 C22 109.1(14) . .
C20 C29 P1 110.1(11) . .
C22 C29 P1 117.1(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 N3 1.941(16) .
Ir1 C1 2.128(17) .
Ir1 C2 2.133(18) .
Ir1 P2 2.285(4) .
Ir1 P1 2.324(4) .
P1 N4 1.715(13) .
P1 C29 1.817(16) .
P1 C27 1.836(15) .
P2 N5 1.671(15) .
P2 C26 1.825(18) .
P2 C28 1.887(19) .
N1 C10 1.356(19) .
N1 C9 1.37(2) .
N2 C17 1.323(18) .
N2 C10 1.337(19) .
N3 C9 1.41(2) .
N3 C17 1.447(19) .
N4 C17 1.321(18) .
N5 C9 1.36(2) .
C1 C2 1.39(2) .
C1 C8 1.52(2) .
C2 C3 1.50(2) .
C3 C4 1.53(2) .
C4 C5 1.528(17) .
C5 C6 1.422(18) .
C6 C7 1.520(17) .
C7 C8 1.57(2) .
C10 C11 1.44(2) .
C11 C12 1.37(2) .
C11 C16 1.44(2) .
C12 C13 1.38(2) .
C13 C14 1.37(2) .
C14 C15 1.42(3) .
C15 C16 1.35(2) .
C18 C27 1.50(2) .
C19 C27 1.56(2) .
C20 C29 1.53(2) .
C21 C28 1.56(3) .
C22 C29 1.53(2) .
C23 C28 1.51(3) .
C24 C26 1.54(3) .
C25 C26 1.51(3) .
