A Pyrene-Based N-Heterocyclic Carbene: Study of Its Coordination Chemistry and Stereoelectronic Properties
Valdés, Hugo; Poyatos, Macarena; Peris, Eduardo; Organometallics 33 (2014) 394–; doi:10.1021/om401134w

data_4082531
_publ_section_title
;
 A Pyrene-Based N-Heterocyclic Carbene: Study of Its Coordination
 Chemistry and Stereoelectronic Properties
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              394
_journal_paper_doi               10.1021/om401134w
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C33 H38 Br Ir N2'
_chemical_formula_sum            'C33 H38 Br Ir N2'
_chemical_formula_weight         734.76
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-11-13
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.674(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3221(3)
_cell_length_b                   21.3617(5)
_cell_length_c                   14.4693(4)
_cell_measurement_reflns_used    8279
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      28.5540
_cell_measurement_theta_min      3.0420
_cell_volume                     2821.76(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector_area_resol_mean 10.4051
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.8903
_diffrn_measurement_details
;
  1 omega  -19.00   25.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.1253  -99.0000   90.0000 44

  2 omega  -13.00   17.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.1253  -57.0000 -180.0000 30

  3 omega  -68.00  -41.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.1253  -57.0000 -180.0000 27

  4 omega  -33.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753   19.0000    0.0000 127

  5 omega    7.00   34.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753   77.0000   90.0000 27

  6 omega   45.00   72.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753   77.0000   90.0000 27

  7 omega    8.00   40.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       12.3753  -57.0000  -30.0000 32
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0149490000
_diffrn_orient_matrix_UB_12      -0.0241897000
_diffrn_orient_matrix_UB_13      0.0341868000
_diffrn_orient_matrix_UB_21      0.0726792000
_diffrn_orient_matrix_UB_22      0.0112566000
_diffrn_orient_matrix_UB_23      0.0144703000
_diffrn_orient_matrix_UB_31      -0.0230862000
_diffrn_orient_matrix_UB_32      0.0197629000
_diffrn_orient_matrix_UB_33      0.0335711000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22604
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.493
_diffrn_reflns_theta_min         2.875
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_description       prism
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.3379
_exptl_crystal_size_mid          0.1486
_exptl_crystal_size_min          0.1169
_refine_diff_density_max         1.415
_refine_diff_density_min         -1.293
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         6991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+8.7576P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5346
_reflns_number_total             6991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om401134w_si_002.cif
_cod_data_source_block           of_6b_(str1540)
_cod_original_cell_volume        2821.75(14)
_cod_database_code               4082531
_chemical_oxdiff_formula         'C35 H45 Cl N2 Ir'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2A(0.052) H2B(0.052) H3A(0.053) H3B(0.053) H4A(0.063) H4B(0.063)
 H5A(0.106) H5B(0.106) H5C(0.106) H6A(0.058) H6B(0.058) H7A(0.066) H7B(0.066)
 H8A(0.099) H8B(0.099) H9A(0.19) H9B(0.19) H9C(0.19) H13(0.064) H14(0.073)
 H15(0.067) H17(0.064) H18(0.06) H20(0.06) H21(0.065) H22(0.057) H26(0.055)
 H27A(0.074) H27B(0.074) H28A(0.124) H28B(0.124) H29(0.069) H30(0.07)
 H31A(0.128) H31B(0.128) H32A(0.093) H32B(0.093) H33(0.059)
 Fixed X: H2A(0.1476) H2B(0.2828) H3A(0.1082) H3B(-0.0129) H4A(0.2154)
 H4B(0.0954) H5A(-0.0834) H5B(0.0326) H5C(0.0413) H6A(0.3414) H6B(0.4572)
 H7A(0.5582) H7B(0.4373) H8A(0.6505) H8B(0.5276) H9A(0.6353) H9B(0.7201)
 H9C(0.7711) H13(0.2361) H14(0.1188) H15(-0.1011) H17(-0.3035) H18(-0.4011)
 H20(-0.3894) H21(-0.276) H22(-0.0565) H26(0.5066) H27A(0.7266) H27B(0.5689)
 H28A(0.6322) H28B(0.7732) H29(0.5611) H30(0.6609) H31A(0.884) H31B(0.8364)
 H32A(0.8287) H32B(0.8596) H33(0.6157)
 Fixed Y: H2A(0.6846) H2B(0.7209) H3A(0.773) H3B(0.7467) H4A(0.8271)
 H4B(0.8005) H5A(0.8567) H5B(0.9014) H5C(0.8858) H6A(0.6006) H6B(0.6425)
 H7A(0.5552) H7B(0.5122) H8A(0.5785) H8B(0.5376) H9A(0.4514) H9B(0.4762)
 H9C(0.4954) H13(0.5153) H14(0.43) H15(0.3958) H17(0.4071) H18(0.4524)
 H20(0.5307) H21(0.6121) H22(0.651) H26(0.6666) H27A(0.7342) H27B(0.7595)
 H28A(0.839) H28B(0.8071) H29(0.8481) H30(0.799) H31A(0.7626) H31B(0.7268)
 H32A(0.6461) H32B(0.6833) H33(0.6204)
 Fixed Z: H2A(-0.0652) H2B(-0.0079) H3A(0.0708) H3B(-0.0115) H4A(-0.0393) H4B(-
 0.1218) H5A(-0.0621) H5B(-0.0921) H5C(0.0148) H6A(0.3444) H6B(0.3091)
 H7A(0.2518) H7B(0.2801) H8A(0.4119) H8B(0.4412) H9A(0.3729) H9B(0.4707)
 H9C(0.3779) H13(0.33) H14(0.3768) H15(0.2883) H17(0.1499) H18(0.0129) H20(-
 0.1095) H21(-0.1662) H22(-0.0842) H26(0.0073) H27A(-0.0129) H27B(-0.0537)
 H28A(0.0225) H28B(0.0795) H29(0.1595) H30(0.2891) H31A(0.2258) H31B(0.3088)
 H32A(0.2313) H32B(0.1442) H33(0.1366)
;
_shelx_hkl_checksum              2156
_shelx_res_checksum              84879
_shelxl_version_number           2013-4