Diametric calix[6]arene gold(i) catalysts for intramolecular cyclopropanations of 1,6-dienynes
Giovanardi, Gabriele; Balestri, Davide; Secchi, Andrea; Cera, Gianpiero; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01074G

data_7158799
_publ_section_title
;
 Diametric calix[6]arene gold(i) catalysts for intramolecular
 cyclopropanations of 1,6-dienynes
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01074G
_journal_year                    2022
_chemical_formula_moiety         'C116 H136 Au2 Cl2 N2 O8 P2, 3(C2 H3 N)'
_chemical_formula_sum            'C122 H145 Au2 Cl2 N5 O8 P2'
_chemical_formula_weight         2336.19
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-21 deposited with the CCDC.	2022-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                68.278(2)
_cell_angle_beta                 84.913(2)
_cell_angle_gamma                85.553(2)
_cell_formula_units_Z            1
_cell_length_a                   12.0018(3)
_cell_length_b                   15.5165(4)
_cell_length_c                   17.7252(4)
_cell_measurement_reflns_used    20710
_cell_measurement_temperature    200
_cell_measurement_theta_max      30.2860
_cell_measurement_theta_min      2.0400
_cell_volume                     3050.85(14)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.00
_diffrn_detector                 'Photon II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -25.75 153.25   1.00    1.00 -25.75   0.00  73.76    --   179
  2  \f   -339.92  20.08   0.20   10.00  19.65  -0.10 -59.25    --  1800
  3  \w    -67.41  -9.01   0.20   10.00    --  -19.75 107.56 -58.15  292
  4  \w    -54.67  21.93   0.20   10.00    --  -19.75  84.97 135.99  383
  5  \w    -82.73  19.47   0.20   10.00    --   -0.10 -59.25  92.08  511
;
_diffrn_measurement_device       'Bruker D8 VENTURE'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0194851000
_diffrn_orient_matrix_UB_12      0.0229666000
_diffrn_orient_matrix_UB_13      -0.0394901000
_diffrn_orient_matrix_UB_21      0.0467383000
_diffrn_orient_matrix_UB_22      -0.0193884000
_diffrn_orient_matrix_UB_23      -0.0167016000
_diffrn_orient_matrix_UB_31      -0.0310572000
_diffrn_orient_matrix_UB_32      -0.0390334000
_diffrn_orient_matrix_UB_33      0.0049874000
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            75557
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.042
_diffrn_source                   microfocus
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       cube
_exptl_crystal_F_000             1198
_exptl_crystal_preparation       'Compound from synthesis'
_exptl_crystal_recrystallization_method
'Slow evaporation of chloroform/acetonitrile mixture'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.979
_refine_diff_density_min         -0.961
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     710
_refine_ls_number_reflns         11536
_refine_ls_number_restraints     209
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0735P)^2^+4.6717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1360
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9936
_reflns_number_total             11536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01074g2.cif
_cod_data_source_block           A_(AuCl)2
_cod_database_code               7158799
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.843
_shelx_estimated_absorpt_t_min   0.703
_olex2_refinement_description
;
1. Others
 Fixed Sof: C83(0.8) H83A(0.8) H83B(0.8) H83C(0.8) C73(0.8) H73A(0.8)
 H73B(0.8) H73C(0.8) C9B(0.5) H9BA(0.5) H9BB(0.5) H9BC(0.5) C7B(0.5) H7BA(0.5)
 H7BB(0.5) H7BC(0.5) C92(0.5) H92A(0.5) H92B(0.5) H92C(0.5) C93(0.8) H93A(0.8)
 H93B(0.8) H93C(0.8) C7C(0.2) H7CA(0.2) H7CB(0.2) H7CC(0.2) C9C(0.2) H9CA(0.2)
 H9CB(0.2) H9CC(0.2) C8C(0.2) H8CA(0.2) H8CB(0.2) H8CC(0.2) C82(0.5) H82A(0.5)
 H82B(0.5) H82C(0.5) C72(0.5) H72A(0.5) H72B(0.5) H72C(0.5) C8B(0.5) H8BA(0.5)
 H8BB(0.5) H8BC(0.5) N1A1(0.5) C1A1(0.5) C2A1(0.5) H2AA(0.5) H2AB(0.5) H2AC(0.5)
 Fixed Uiso: H11(0.044) H41(0.042) H23(0.042) HM1A(0.043) HM1B(0.043)
 H21(0.04) H43(0.045) H91(0.051) H121(0.052) H111(0.053) H81(0.049) H22(0.047)
 H42(0.054) HM2A(0.066) HM2B(0.066) H141(0.066) H24A(0.062) H24B(0.062)
 HM1C(0.058) HM1D(0.058) H10A(0.09) H10B(0.09) H10C(0.09) H161(0.077)
 H26A(0.069) H26B(0.069) H01A(0.086) H01B(0.086) H01C(0.086) H181(0.082)
 H201(0.085) H28A(0.078) H28B(0.078) H151(0.085) H01G(0.076) H25A(0.076)
 H25B(0.076) H171(0.094) H29A(0.083) H29B(0.083) H27A(0.084) H27B(0.084)
 H231(0.092) H221(0.101) H83A(0.116) H83B(0.116) H83C(0.116) H211(0.105)
 H3AA(0.154) H3AB(0.154) H3AC(0.154) H30A(0.097) H30B(0.097) H73A(0.116)
 H73B(0.116) H73C(0.116) H31A(0.15) H31B(0.15) H31C(0.15) H9BA(0.15) H9BB(0.15)
 H9BC(0.15) H7BA(0.146) H7BB(0.146) H7BC(0.146) H92A(0.147) H92B(0.147)
 H92C(0.147) H93A(0.123) H93B(0.123) H93C(0.123) H7CA(0.117) H7CB(0.117)
 H7CC(0.117) H9CA(0.118) H9CB(0.118) H9CC(0.118) H8CA(0.121) H8CB(0.121)
 H8CC(0.121) H82A(0.143) H82B(0.143) H82C(0.143) H72A(0.149) H72B(0.149)
 H72C(0.149) H8BA(0.151) H8BB(0.151) H8BC(0.151) H2AA(0.151) H2AB(0.151)
 H2AC(0.151)
 Fixed X: H11(0.8079) H41(0.7906) H23(0.7228) HM1A(0.9261) HM1B(0.9146)
 H21(0.8636) H43(0.5023) H91(0.7973) H121(0.8793) H111(0.847) H81(0.8232)
 H22(0.8376) H42(0.5425) HM2A(0.3687) HM2B(0.3708) H141(0.6543) H24A(1.0045)
 H24B(0.9767) HM1C(0.8457) HM1D(0.7341) H10A(0.5446) H10B(0.5808) H10C(0.451)
 H161(0.3382) H26A(0.8219) H26B(0.9425) H01A(0.9265) H01B(0.932) H01C(0.8436)
 H181(0.5966) H201(0.6416) H28A(0.761) H28B(0.8469) H151(0.4638) H01G(0.9595)
 H25A(1.0257) H25B(0.9027) H171(0.4075) H29A(0.9558) H29B(0.8554) H27A(0.8819)
 H27B(0.988) H231(0.9727) H221(0.8203) H83A(0.3806) H83B(0.3781) H83C(0.4543)
 H211(0.6588) H3AA(0.7474) H3AB(0.7512) H3AC(0.6345) H30A(0.8363) H30B(0.7349)
 H73A(0.537) H73B(0.4291) H73C(0.4298) H31A(0.7999) H31B(0.8336) H31C(0.9257)
 H9BA(0.7671) H9BB(0.7613) H9BC(0.6511) H7BA(0.7474) H7BB(0.7358) H7BC(0.634)
 H92A(0.885) H92B(0.9136) H92C(0.8281) H93A(0.5402) H93B(0.63) H93C(0.6453)
 H7CA(0.4448) H7CB(0.4081) H7CC(0.359) H9CA(0.6209) H9CB(0.5195) H9CC(0.6279)
 H8CA(0.4542) H8CB(0.4552) H8CC(0.5684) H82A(0.8706) H82B(0.8423) H82C(0.7514)
 H72A(0.6357) H72B(0.7311) H72C(0.6401) H8BA(0.9145) H8BB(0.9173) H8BC(0.9006)
 H2AA(0.6334) H2AB(0.5168) H2AC(0.6054)
 Fixed Y: H11(0.7119) H41(0.5607) H23(0.2712) HM1A(0.4338) HM1B(0.3341)
 H21(0.5745) H43(0.3525) H91(1.011) H121(0.8526) H111(1.0145) H81(0.8502)
 H22(0.4594) H42(0.5618) HM2A(0.4396) HM2B(0.525) H141(1.3101) H24A(0.272)
 H24B(0.2803) HM1C(0.3499) HM1D(0.3219) H10A(0.4964) H10B(0.3978) H10C(0.4266)
 H161(1.2235) H26A(0.1303) H26B(0.1306) H01A(0.5487) H01B(0.4424) H01C(0.4771)
 H181(1.0407) H201(1.1621) H28A(-0.02) H28B(-0.1083) H151(1.3408) H01G(1.2342)
 H25A(0.1255) H25B(0.1351) H171(1.0736) H29A(-0.0266) H29B(0.0506) H27A(-
 0.0189) H27B(-0.019) H231(1.2768) H221(1.2633) H83A(0.1587) H83B(0.2678)
 H83C(0.1976) H211(1.2071) H3AA(0.8077) H3AB(0.6967) H3AC(0.7535) H30A(-0.1386)
 H30B(-0.0624) H73A(0.2507) H73B(0.3011) H73C(0.1926) H31A(-0.0832) H31B(0.018)
 H31C(-0.0663) H9BA(0.6991) H9BB(0.6901) H9BC(0.6782) H7BA(0.4613) H7BB(0.5649)
 H7BC(0.5229) H92A(0.6469) H92B(0.5765) H92C(0.6638) H93A(0.0784) H93B(0.1212)
 H93C(0.129) H7CA(0.2836) H7CB(0.3318) H7CC(0.2346) H9CA(0.192) H9CB(0.1241)
 H9CC(0.1096) H8CA(0.1025) H8CB(0.182) H8CC(0.1236) H82A(0.4405) H82B(0.4969)
 H82C(0.4321) H72A(0.5551) H72B(0.6239) H72C(0.6548) H8BA(0.6065) H8BB(0.4991)
 H8BC(0.5777) H2AA(0.1888) H2AB(0.1514) H2AC(0.1871)
 Fixed Z: H11(0.3885) H41(0.2905) H23(0.6336) HM1A(0.6132) HM1B(0.6081)
 H21(0.5033) H43(0.7817) H91(0.311) H121(0.1335) H111(0.0814) H81(0.362)
 H22(0.18) H42(0.0839) HM2A(0.2458) HM2B(0.1603) H141(0.1584) H24A(0.5142)
 H24B(0.4248) HM1C(0.3139) HM1D(0.3719) H10A(0.3809) H10B(0.4468) H10C(0.4336)
 H161(0.2042) H26A(0.6021) H26B(0.6338) H01A(0.7327) H01B(0.7402) H01C(0.7973)
 H181(0.2099) H201(0.0335) H28A(0.7025) H28B(0.7274) H151(0.1761) H01G(0.0287)
 H25A(0.507) H25B(0.4757) H171(0.2283) H29A(0.7848) H29B(0.7695) H27A(0.5908)
 H27B(0.6394) H231(-0.1153) H221(-0.1803) H83A(0.7816) H83B(0.7633)
 H83C(0.8318) H211(-0.1098) H3AA(0.6344) H3AB(0.674) H3AC(0.6493) H30A(0.873)
 H30B(0.857) H73A(0.5909) H73B(0.6194) H73C(0.6352) H31A(0.9813) H31B(0.9204)
 H31C(0.9428) H9BA(-0.0472) H9BB(0.046) H9BC(0.0067) H7BA(-0.0149) H7BB(-
 0.0802) H7BC(-0.0152) H92A(-0.0237) H92B(0.0653) H92C(0.0551) H93A(0.7522)
 H93B(0.7884) H93C(0.6955) H7CA(0.6064) H7CB(0.671) H7CC(0.6821) H9CA(0.6234)
 H9CB(0.6596) H9CC(0.7102) H8CA(0.7939) H8CB(0.8311) H8CC(0.8227) H82A(0.0457)
 H82B(-0.0468) H82C(0.0157) H72A(-0.0372) H72B(-0.0884) H72C(-0.0305) H8BA(-
 0.0146) H8BB(0.0433) H8BC(0.0822) H2AA(0.3737) H2AB(0.4213) H2AC(0.4643)
;
_shelx_res_checksum              99650
_olex2_exptl_crystal_mounting_method
'Slow evaporation from chloroform/acetonitrile solvent mixture'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.444
_oxdiff_exptl_absorpt_empirical_full_min 0.720