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_4082530
_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 Cl N2 Rh'
_chemical_formula_sum            'C33 H38 Cl N2 Rh'
_chemical_formula_weight         601.01
_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
_atom_sites_solution_primary     direct
_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                 90.7989(6)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   18.20666(12)
_cell_length_b                   21.18239(13)
_cell_length_c                   21.55681(15)
_cell_measurement_temperature    200(2)
_cell_volume                     8312.80(9)
_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
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      199.95(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            77781
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.660
_diffrn_reflns_theta_min         2.925
_exptl_absorpt_coefficient_mu    6.045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60777
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_description       prism
_exptl_crystal_F_000             3744
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.116
_refine_diff_density_max         2.365
_refine_diff_density_min         -1.363
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1035
_refine_ls_number_reflns         16357
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0813P)^2^+14.6543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13337
_reflns_number_total             16357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om401134w_si_002.cif
_cod_data_source_block           of_5a_(str1534)
_cod_depositor_comments
;

2026-05-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C99 H114 Cl3 N6 Rh3'
_cod_original_formula_weight         1803.04
_cod_original_formula_moiety         '3(C33 H38 Cl N2 Rh)'
_cod_original_formula_units_Z            4
_cod_database_code               4082530
_olex2_refinement_description
;
1. Others
 Fixed Sof: H4AA(0.5) H4AB(0.5) H4BC(0.5) H4BD(0.5) C5A(0.5) H5AA(0.5)
 H5AB(0.5) H5AC(0.5) H36A(0.5) H36B(0.5) H36C(0.5) H36D(0.5) C37A(0.5)
 H37A(0.5) H37B(0.5) C38A(0.5) H38A(0.5) H38B(0.5) H38C(0.5) C5B(0.5) H5BA(0.5)
 H5BB(0.5) H5BC(0.5) C37B(0.5) H37C(0.5) H37D(0.5) C38B(0.5) H38D(0.5)
 H38E(0.5) H38F(0.5)
 Fixed Uiso: H2A(0.063) H2B(0.063) H3A(0.073) H3B(0.073) H4AA(0.14) H4AB(0.14)
 H4BC(0.14) H4BD(0.14) H5AA(0.149) H5AB(0.149) H5AC(0.149) H6A(0.06) H6B(0.06)
 H7A(0.067) H7B(0.067) H8A(0.091) H8B(0.091) H9A(0.137) H9B(0.137) H9C(0.137)
 H12(0.072) H13(0.085) H14(0.079) H17(0.071) H18(0.067) H21(0.067) H22(0.073)
 H23(0.064) H26(0.069) H27(0.067) H28A(0.076) H28B(0.076) H29A(0.094)
 H29B(0.094) H30(0.07) H31(0.078) H32A(0.095) H32B(0.095) H33A(0.078)
 H33B(0.078) H35A(0.08) H35B(0.08) H36A(0.107) H36B(0.107) H36C(0.107)
 H36D(0.107) H37A(0.143) H37B(0.143) H38A(0.33) H38B(0.33) H38C(0.33)
 H39A(0.065) H39B(0.065) H40A(0.072) H40B(0.072) H41A(0.102) H41B(0.102)
 H42A(0.173) H42B(0.173) H42C(0.173) H45(0.073) H46(0.08) H47(0.074) H51(0.074)
 H52(0.076) H55(0.083) H56(0.086) H57(0.073) H60(0.086) H61A(0.093) H61B(0.093)
 H62A(0.102) H62B(0.102) H63(0.078) H64(0.08) H65A(0.098) H65B(0.098)
 H66A(0.089) H66B(0.089) H67(0.084) H69A(0.071) H69B(0.071) H70A(0.074)
 H70B(0.074) H71A(0.103) H71B(0.103) H72A(0.172) H72B(0.172) H72C(0.172)
 H73A(0.063) H73B(0.063) H74A(0.073) H74B(0.073) H75A(0.097) H75B(0.097)
 H76A(0.156) H76B(0.156) H76C(0.156) H79(0.071) H80(0.08) H81(0.078) H84(0.079)
 H85(0.082) H88(0.085) H89(0.087) H90(0.076) H93(0.087) H94(0.09) H95A(0.127)
 H95B(0.127) H96A(0.08) H96B(0.08) H97(0.069) H98(0.074) H99A(0.096)
 H99B(0.096) H10A(0.133) H10B(0.133) H5BA(0.107) H5BB(0.107) H5BC(0.107)
 H37C(0.077) H37D(0.077) H38D(0.107) H38E(0.107) H38F(0.107)
 Fixed X: H2A(0.2474) H2B(0.2448) H3A(0.361) H3B(0.3511) H4AA(0.2267)
 H4AB(0.2982) H4BC(0.247) H4BD(0.24) H5AA(0.3147) H5AB(0.2565) H5AC(0.229)
 H6A(0.4504) H6B(0.3844) H7A(0.3683) H7B(0.3028) H8A(0.4315) H8B(0.3584)
 H9A(0.2948) H9B(0.3625) H9C(0.3691) H12(0.4818) H13(0.5509) H14(0.5582)
 H17(0.5315) H18(0.4746) H21(0.3939) H22(0.3176) H23(0.3006) H26(0.1775)
 H27(0.2225) H28A(0.1997) H28B(0.1455) H29A(0.2182) H29B(0.2864) H30(0.3263)
 H31(0.2692) H32A(0.145) H32B(0.1402) H33A(0.1337) H33B(0.0864) H35A(0.2911)
 H35B(0.224) H36A(0.3031) H36B(0.3717) H36C(0.3706) H36D(0.3106) H37A(0.2289)
 H37B(0.2897) H38A(0.3668) H38B(0.2907) H38C(0.3138) H39A(0.414) H39B(0.411)
 H40A(0.2992) H40B(0.2895) H41A(0.3206) H41B(0.3879) H42A(0.4543) H42B(0.4221)
 H42C(0.3853) H45(0.3557) H46(0.3369) H47(0.2611) H51(0.1798) H52(0.1246)
 H55(0.1046) H56(0.1208) H57(0.1933) H60(0.4992) H61A(0.5678) H61B(0.5673)
 H62A(0.4827) H62B(0.5196) H63(0.3824) H64(0.3615) H65A(0.5113) H65B(0.4527)
 H66A(0.5237) H66B(0.4379) H67(0.4583) H69A(-0.0674) H69B(-0.1294) H70A(-
 0.0515) H70B(0.0122) H71A(-0.1271) H71B(-0.0642) H72A(0.0082) H72B(-0.0722)
 H72C(-0.039) H73A(0.0942) H73B(0.0893) H74A(-0.0096) H74B(-0.0174)
 H75A(0.1072) H75B(0.102) H76A(0.0099) H76B(0.0777) H76C(0.0076) H79(0.0346)
 H80(0.0217) H81(-0.0583) H84(-0.1416) H85(-0.2049) H88(-0.235) H89(-0.2266)
 H90(-0.1535) H93(0.0052) H94(0.0466) H95A(0.1572) H95B(0.1828) H96A(0.2272)
 H96B(0.2314) H97(0.1614) H98(0.1078) H99A(0.1676) H99B(0.0826) H10A(0.0779)
 H10B(0.1477) H5BA(0.3315) H5BB(0.2546) H5BC(0.3219) H37C(0.2486) H37D(0.3271)
 H38D(0.3041) H38E(0.3221) H38F(0.3831)
 Fixed Y: H2A(0.6827) H2B(0.719) H3A(0.7676) H3B(0.7378) H4AA(0.7942)
 H4AB(0.8326) H4BC(0.8203) H4BD(0.7923) H5AA(0.8522) H5AB(0.8942) H5AC(0.836)
 H6A(0.574) H6B(0.6164) H7A(0.4864) H7B(0.5289) H8A(0.5007) H8B(0.4593)
 H9A(0.5477) H9B(0.5299) H9C(0.5879) H12(0.4959) H13(0.4081) H14(0.3758)
 H17(0.3927) H18(0.4474) H21(0.5336) H22(0.6181) H23(0.6507) H26(0.6572)
 H27(0.6147) H28A(0.6482) H28B(0.7) H29A(0.7643) H29B(0.7168) H30(0.7981)
 H31(0.8427) H32A(0.8403) H32B(0.7963) H33A(0.7597) H33B(0.7332) H35A(0.3637)
 H35B(0.4071) H36A(0.4976) H36B(0.4536) H36C(0.448) H36D(0.4918) H37A(0.463)
 H37B(0.4113) H38A(0.4834) H38B(0.4981) H38C(0.5375) H39A(0.2632) H39B(0.3035)
 H40A(0.2182) H40B(0.2623) H41A(0.1627) H41B(0.2085) H42A(0.1677) H42B(0.11)
 H42C(0.1288) H45(0.3427) H46(0.3837) H47(0.4695) H51(0.5519) H52(0.6008)
 H55(0.6123) H56(0.5764) H57(0.4893) H60(0.3123) H61A(0.2319) H61B(0.2241)
 H62A(0.1474) H62B(0.1349) H63(0.1406) H64(0.1946) H65A(0.2175) H65B(0.2353)
 H66A(0.323) H66B(0.3343) H67(0.3689) H69A(0.3572) H69B(0.4036) H70A(0.4909)
 H70B(0.4448) H71A(0.4603) H71B(0.4134) H72A(0.4935) H72B(0.5128) H72C(0.5439)
 H73A(0.2783) H73B(0.3163) H74A(0.2563) H74B(0.2239) H75A(0.2072) H75B(0.1766)
 H76A(0.1124) H76B(0.105) H76C(0.1458) H79(0.3491) H80(0.3889) H81(0.4719)
 H84(0.5539) H85(0.6013) H88(0.6117) H89(0.576) H90(0.4892) H93(0.1969)
 H94(0.1449) H95A(0.1548) H95B(0.1493) H96A(0.2456) H96B(0.2364) H97(0.323)
 H98(0.3756) H99A(0.3245) H99B(0.3419) H10A(0.2455) H10B(0.2236) H5BA(0.8552)
 H5BB(0.8864) H5BC(0.8876) H37C(0.4961) H37D(0.5306) H38D(0.4047) H38E(0.4646)
 H38F(0.4376)
 Fixed Z: H2A(0.7966) H2B(0.7315) H3A(0.7607) H3B(0.8284) H4AA(0.8219)
 H4AB(0.8447) H4BC(0.7715) H4BD(0.8392) H5AA(0.7329) H5AB(0.7696) H5AC(0.728)
 H6A(0.5978) H6B(0.5711) H7A(0.6063) H7B(0.579) H8A(0.5091) H8B(0.5034)
 H9A(0.465) H9B(0.4218) H9C(0.4691) H12(0.6458) H13(0.6743) H14(0.777)
 H17(0.8868) H18(0.9621) H21(0.9947) H22(0.9711) H23(0.8694) H26(0.6544)
 H27(0.5694) H28A(0.4728) H28B(0.5006) H29A(0.4511) H29B(0.4545) H30(0.5183)
 H31(0.5938) H32A(0.6021) H32B(0.5418) H33A(0.6673) H33B(0.6099) H35A(1.0998)
 H35B(1.0772) H36A(1.0754) H36B(1.0976) H36C(1.0981) H36D(1.0658) H37A(1.1676)
 H37B(1.1865) H38A(1.2118) H38B(1.2451) H38C(1.1851) H39A(0.928) H39B(0.8651)
 H40A(0.9051) H40B(0.8454) H41A(0.8112) H41B(0.7973) H42A(0.8755) H42B(0.8358)
 H42C(0.9002) H45(0.7971) H46(0.6981) H47(0.682) H51(0.7218) H52(0.8014)
 H55(0.9136) H56(1.0145) H57(1.0357) H60(1.0002) H61A(1.0817) H61B(1.008)
 H62A(1.0089) H62B(1.0755) H63(1.0734) H64(1.1571) H65A(1.164) H65B(1.2158)
 H66A(1.1692) H66B(1.1801) H67(1.0775) H69A(0.7436) H69B(0.717) H70A(0.7335)
 H70B(0.7584) H71A(0.8178) H71B(0.8424) H72A(0.8725) H72B(0.8948) H72C(0.8337)
 H73A(0.5858) H73B(0.5218) H74A(0.4879) H74B(0.5548) H75A(0.4753) H75B(0.5428)
 H76A(0.5108) H76B(0.4649) H76C(0.4442) H79(0.4499) H80(0.3501) H81(0.3297)
 H84(0.3652) H85(0.4416) H88(0.5519) H89(0.6537) H90(0.6788) H93(0.8047)
 H94(0.7253) H95A(0.6771) H95B(0.748) H96A(0.7505) H96B(0.6771) H97(0.6665)
 H98(0.7403) H99A(0.8338) H99B(0.8401) H10A(0.874) H10B(0.8355) H5BA(0.8672)
 H5BB(0.8475) H5BC(0.8005) H37C(1.164) H37D(1.1626) H38D(1.2091) H38E(1.2519)
 H38F(1.2062)
;
_shelx_hkl_checksum              9281
_shelx_res_checksum              61905
_shelxl_version_number           2013-4