A crystalline cyclic (alkyl)(amino)carbene with a 1,1‘-ferrocenylene backbone
Volk, Julia; Heinz, Myron; Leibold, Michael; Bruhn, Clemens; Bens, Tobias; Sarkar, Biprajit; Holthausen, Max C.; Siemeling, Ulrich; Chemical Communications  (2022) –; doi:10.1039/D2CC03871D

data_7130581
_publ_section_title
;
 A crystalline cyclic (alkyl)(amino)carbene with a
 1,1&#x2018;-ferrocenylene backbone
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03871D
_journal_year                    2022
_chemical_formula_moiety         'C33 H29 Fe N'
_chemical_formula_sum            'C33 H29 Fe N'
_chemical_formula_weight         495.42
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-01 deposited with the CCDC.	2022-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.528(2)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   24.8763(7)
_cell_length_b                   11.9118(2)
_cell_length_c                   24.1323(7)
_cell_measurement_reflns_used    53248
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.81
_cell_measurement_theta_min      4.00
_cell_volume                     7144.0(3)
_computing_cell_refinement
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.175.0 (STOE, 2021)
;
_computing_data_reduction
;
X-Area Integrate 2.5.1.0 (STOE, 2021)
X-Area LANA 2.6.2.0 (STOE, 2021)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 2.0, Darmstadt 2021
;
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 Pilatus200K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
 1492 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '1.2 mm, 0.6 diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            50485
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.673
_diffrn_reflns_theta_min         3.557
_diffrn_source                   Cu-Genix
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_target            Cu
_diffrn_source_type              'Genix Cu 3D HF'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    5.234
_exptl_absorpt_correction_T_max  0.6929
_exptl_absorpt_correction_T_min  0.0852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in: F. R. Ahmed (Editor), "Crystallographic
Computing", Munksgaard, Copenhagen (1970), 255 - 270. Afterwards scaling of
reflection intensities was performed within STOE LANA. J. Koziskova, F. Hahn,
J. Richter, J. Kozisek, Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136-140.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3120
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     952
_refine_ls_number_reflns         13668
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^+5.0515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11715
_reflns_number_total             13668
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03871d2.cif
_cod_data_source_block           sv1216
_cod_database_code               7130581
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.711
_shelx_estimated_absorpt_t_min   0.192
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C34(H34), C67(H67)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C52(H52A,H52B), C85(H85A,H85B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C17(H17), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33), C37(H37), C38(H38), C39(H39),
 C40(H40), C42(H42), C43(H43), C44(H44), C45(H45), C48(H48), C50(H50), C56(H56),
  C57(H57), C58(H58), C59(H59), C60(H60), C62(H62), C63(H63), C64(H64),
 C65(H65), C66(H66), C70(H70), C71(H71), C72(H72), C73(H73), C75(H75), C76(H76),
  C77(H77), C78(H78), C81(H81), C83(H83), C89(H89), C90(H90), C91(H91),
 C92(H92), C93(H93), C95(H95), C96(H96), C97(H97), C98(H98), C99(H99)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C53(H53A,H53B,H53C), C54(H54A,H54B,
 H54C), C86(H86A,H86B,H86C), C87(H87A,H87B,H87C)
;
_shelx_res_checksum              71338
_shelx_hkl_checksum              22976
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance          '40.0 mm'
_stoe_detector_pixelsize_x       '0.172 mm'
_stoe_detector_pixelsize_y       '0.172 mm'
_stoe_detector_size_x            '7.0 cm'
_stoe_detector_size_y            '8.4 cm'
_stoe_evaluation_integration_a   6.0
_stoe_evaluation_integration_b   0.0
_stoe_evaluation_integration_ems 0.010
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max -
_stoe_evaluation_lana_bos_l_odd_max -
_stoe_evaluation_lana_completeness 97.9
_stoe_evaluation_lana_dxs_max_order 1
_stoe_evaluation_lana_dys_max_order 1
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 143.4
_stoe_evaluation_lana_max_2theta_desired 143.4
_stoe_evaluation_lana_mean_redundancy 3.7
_stoe_evaluation_lana_number_refls_after_or 50163
_stoe_evaluation_lana_number_refls_outliers 0
_stoe_evaluation_lana_number_refls_total 63541
_stoe_evaluation_lana_number_refls_unique 13670
_stoe_evaluation_lana_number_refls_written 50163
_stoe_evaluation_lana_or_c1      0.035
_stoe_evaluation_lana_or_c2      0
_stoe_evaluation_lana_or_c3      0
_stoe_evaluation_lana_or_c4      0.7
_stoe_evaluation_lana_point_group 2/m
_stoe_evaluation_lana_table
;
2Theta          11.9   27.5   43.1   58.7   74.3   89.9  105.5  121.1  136.7
<Resolution>    2.42   3.10   0.00   0.00   1.62   0.00   0.00   1.89   5.16
N(total)         182   1097   2989   6724  14626  14240  10333   9581   3769
<Redundancy>     1.9    2.5    3.2    3.6    5.2    4.6    2.9    2.6    1.7
Complet. [%%]       -      -      -      -      -      -      -      -      -
<I/sigma>    16967.522334.728036.428345.822038.013654.1 8144.5 7818.5 2033.5
R(int)         0.000  0.000  0.000  0.000  0.000  0.000  0.000  0.000  0.000
;
_stoe_measurement_identifier     sv1216
_stoe_measurement_max_exposure_per_frame '60.0 s'
_stoe_measurement_mean_exposure_per_frame '60.0 s'
_stoe_measurement_min_exposure_per_frame '60.0 s'
_stoe_measurement_total_exposure_time '24.9 h'
_stoe_measurement_total_frame_number 1492
_stoe_measurement_total_run_number 28
_stoe_measurement_tube_power     '30.0 W'