A helically twisted imine macrocycle that allows for determining the absolute configuration of appha-amino carboxylates
Min Jun Kim; Ye Rin Choi; Hae-Geun Jeon; Philjae Kang; Moon-Gun Choi; Kyu-Sung Jeong; Chem.Commun. 49 (2013) 11412–; doi:10.1039/c3cc46754f

data_7110084
_publ_section_title
;
 A helically twisted imine macrocycle that allows for determining the
 absolute configuration of appha-amino carboxylates
;
_journal_name_full               Chem.Commun.
_journal_page_first              11412
_journal_paper_doi               10.1039/c3cc46754f
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C84 H80 N6 O4, C16 H36 N, C2 H3 O2'
_chemical_formula_sum            'C102 H119 N7 O6'
_chemical_formula_weight         1539.03
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-10-10
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0521(4)
_cell_length_b                   16.1874(4)
_cell_length_c                   38.9167(10)
_cell_measurement_reflns_used    9718
_cell_measurement_temperature    140.0
_cell_measurement_theta_max      75.60
_cell_measurement_theta_min      2.27
_cell_volume                     10112.2(4)
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      140.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            321916
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         80.00
_diffrn_reflns_theta_min         2.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.486
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1038 before and 0.0790 after correction.
The Ratio of minimum to maximum transmission is 0.8996.
The \l/2 correction factor is 0.0015.
;
_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    1.011
_exptl_crystal_description       block
_exptl_crystal_F_000             3312
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.428
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 5211 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.12(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1057
_refine_ls_number_reflns         21096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1121P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.1956
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                14154
_reflns_number_total             21096
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc46754f.txt
_cod_data_source_block           cu_moon115_0m
_cod_database_code               7110084
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H6(0.047) H3(0.045) H43(0.055) H54(0.046) H26(0.057) H57(0.048)
 H46(0.051) H38(0.055) H34(0.047) H14(0.052) H23(0.054) H20(0.053) H18(0.053)
 H88(0.058) H47(0.049) H29(0.054) H60A(0.084) H60B(0.084) H60C(0.084)
 H40(0.056) H58(0.047) H35(0.05) H87(0.058) H11(0.055) H62A(0.065) H62B(0.065)
 H62C(0.065) H9(0.057) H49A(0.102) H49B(0.102) H49C(0.102) H90A(0.087)
 H90B(0.087) H15(0.052) H10A(0.071) H10B(0.071) H92A(0.076) H92B(0.076)
 H89A(0.07) H89B(0.07) H10C(0.062) H10D(0.062) H31(0.051) H91A(0.085)
 H91B(0.085) H11A(0.075) H11B(0.075) H11C(0.061) H11D(0.061) H80A(0.109)
 H80B(0.109) H80C(0.109) H10E(0.058) H10F(0.058) H82A(0.114) H82B(0.114)
 H82C(0.114) H81A(0.102) H81B(0.102) H81C(0.102) H11E(0.076) H11F(0.076)
 H10G(0.136) H10H(0.136) H10I(0.136) H11G(0.111) H11H(0.111) H11I(0.111)
 H84A(0.126) H84B(0.126) H84C(0.126) H10J(0.071) H10K(0.071) H51A(0.115)
 H51B(0.115) H51C(0.115) H10L(0.087) H10M(0.087) H11J(0.115) H11K(0.115)
 H78A(0.122) H78B(0.122) H78C(0.122) H77A(0.128) H77B(0.128) H77C(0.128)
 H10N(0.08) H10O(0.08) H72A(0.163) H72B(0.163) H72C(0.163) H86A(0.133)
 H86B(0.133) H86C(0.133) H10P(0.083) H10Q(0.083) H10R(0.08) H10S(0.08)
 H10T(0.176) H10U(0.176) H10V(0.176) H85A(0.131) H85B(0.131) H85C(0.131)
 H11L(0.21) H11M(0.21) H11N(0.21) H74A(0.35) H74B(0.35) H74C(0.35) H76A(0.153)
 H76B(0.153) H76C(0.153) H95A(0.118) H95B(0.118) H95C(0.118) H73A(0.273)
 H73B(0.273) H73C(0.273)
 Fixed X: H6(-0.8642) H3(-0.8959) H43(-0.7644) H54(-0.7484) H26(-0.6629) H57(-
 0.6717) H46(-0.8534) H38(-0.4641) H34(-0.4941) H14(-0.9958) H23(-0.6254) H20(-
 0.9773) H18(-1.0384) H88(-0.6638) H47(-0.8578) H29(-0.6872) H60A(-0.8467)
 H60B(-0.7577) H60C(-0.8328) H40(-0.5492) H58(-0.6483) H35(-0.4647) H87(-
 0.8448) H11(-0.9556) H62A(-0.7434) H62B(-0.7463) H62C(-0.6605) H9(-0.8441)
 H49A(-0.7683) H49B(-0.696) H49C(-0.6773) H90A(-0.7123) H90B(-0.6614) H15(-
 1.0187) H10A(-0.8707) H10B(-0.8236) H92A(-0.8431) H92B(-0.7435) H89A(-0.664)
 H89B(-0.7637) H10C(-0.7068) H10D(-0.7682) H31(-0.553) H91A(-0.7871) H91B(-
 0.8399) H11A(-0.5816) H11B(-0.5393) H11C(-0.6313) H11D(-0.6975) H80A(-0.5835)
 H80B(-0.5044) H80C(-0.5284) H10E(-0.8756) H10F(-0.8248) H82A(-0.4286) H82B(-
 0.4498) H82C(-0.5235) H81A(-0.3862) H81B(-0.3595) H81C(-0.3488) H11E(-0.6689)
 H11F(-0.7142) H10G(-0.9523) H10H(-0.9645) H10I(-1.0394) H11G(-0.6063) H11H(-
 0.6005) H11I(-0.5176) H84A(-0.6102) H84B(-0.5738) H84C(-0.5207) H10J(-0.7246)
 H10K(-0.7787) H51A(-0.8919) H51B(-0.8053) H51C(-0.8471) H10L(-0.761) H10M(-
 0.8349) H11J(-0.609) H11K(-0.6841) H78A(-0.9012) H78B(-0.8805) H78C(-0.8132)
 H77A(-0.799) H77B(-0.8662) H77C(-0.8771) H10N(-0.9426) H10O(-0.9898) H72A(-
 1.1207) H72B(-1.1569) H72C(-1.1787) H86A(-0.7305) H86B(-0.7009) H86C(-0.7391)
 H10P(-0.6204) H10Q(-0.6153) H10R(-0.8304) H10S(-0.8828) H10T(-0.9313) H10U(-
 0.8768) H10V(-0.852) H85A(-0.5074) H85B(-0.5664) H85C(-0.5873) H11L(-0.7569)
 H11M(-0.7511) H11N(-0.6864) H74A(-1.1208) H74B(-1.106) H74C(-1.0304) H76A(-
 1.0218) H76B(-1.006) H76C(-1.0321) H95A(-0.6372) H95B(-0.6484) H95C(-0.7077)
 H73A(-0.9603) H73B(-1.0376) H73C(-0.9804)
 Fixed Y: H6(-0.9103) H3(-0.9059) H43(-1.226) H54(-0.7917) H26(-1.1761) H57(-
 0.9147) H46(-1.1128) H38(-1.3675) H34(-1.4487) H14(-0.6177) H23(-1.1485) H20(-
 0.8364) H18(-0.6498) H88(-1.0119) H47(-1.0277) H29(-1.2768) H60A(-0.6967)
 H60B(-0.6527) H60C(-0.6075) H40(-1.1655) H58(-0.987) H35(-1.4259) H87(-1.0087)
 H11(-0.6625) H62A(-0.8618) H62B(-0.7738) H62C(-0.8072) H9(-0.8548) H49A(-
 1.3685) H49B(-1.4182) H49C(-1.329) H90A(-0.9521) H90B(-1.0202) H15(-0.6126)
 H10A(-1.4062) H10B(-1.4372) H92A(-1.1281) H92B(-1.1315) H89A(-0.8941) H89B(-
 0.8932) H10C(-1.4431) H10D(-1.3943) H31(-1.4384) H91A(-1.0791) H91B(-1.0079)
 H11A(-1.4741) H11B(-1.5468) H11C(-1.4839) H11D(-1.435) H80A(-1.3004) H80B(-
 1.3019) H80C(-1.2189) H10E(-1.5455) H10F(-1.5739) H82A(-1.4188) H82B(-1.4192)
 H82C(-1.422) H81A(-1.2116) H81B(-1.2967) H81C(-1.2852) H11E(-1.6071) H11F(-
 1.5446) H10G(-1.3955) H10H(-1.345) H10I(-1.3993) H11G(-1.5574) H11H(-1.6395)
 H11I(-1.5899) H84A(-1.5368) H84B(-1.5387) H84C(-1.4976) H10J(-1.6396) H10K(-
 1.6159) H51A(-1.2126) H51B(-1.1934) H51C(-1.2827) H10L(-1.3998) H10M(-1.3431)
 H11J(-1.6026) H11K(-1.54) H78A(-0.8063) H78B(-0.7212) H78C(-0.7622) H77A(-
 0.6386) H77B(-0.5929) H77C(-0.593) H10N(-1.5177) H10O(-1.484) H72A(-0.7979)
 H72B(-0.7163) H72C(-0.7363) H86A(-1.3814) H86B(-1.4669) H86C(-1.4655) H10P(-
 1.6519) H10Q(-1.5535) H10R(-1.515) H10S(-1.4453) H10T(-1.4383) H10U(-1.3837)
 H10V(-1.4779) H85A(-1.3733) H85B(-1.4081) H85C(-1.3215) H11L(-1.6764) H11M(-
 1.6227) H11N(-1.6962) H74A(-0.6054) H74B(-0.5774) H74C(-0.5758) H76A(-0.652)
 H76B(-0.6562) H76C(-0.7378) H95A(-0.9468) H95B(-1.0146) H95C(-0.9351) H73A(-
 0.6457) H73B(-0.6667) H73C(-0.7396)
 Fixed Z: H6(0.0451) H3(-0.0263) H43(-0.152) H54(-0.1519) H26(0.0361) H57(-
 0.0479) H46(-0.048) H38(-0.1006) H34(0.0269) H14(0.0517) H23(-0.0317) H20(-
 0.142) H18(-0.0779) H88(-0.2171) H47(-0.1632) H29(0.1526) H60A(-0.1413) H60B(-
 0.144) H60C(-0.1246) H40(-0.1511) H58(-0.1636) H35(-0.0313) H87(-0.2178)
 H11(0.1184) H62A(-0.0082) H62B(0.0106) H62C(-0.0051) H9(0.1669) H49A(-0.1455)
 H49B(-0.1262) H49C(-0.1422) H90A(-0.3059) H90B(-0.2845) H15(-0.0074) H10A(-
 0.0378) H10B(-0.0717) H92A(-0.2518) H92B(-0.2511) H89A(-0.2529) H89B(-0.254)
 H10C(0.0232) H10D(-0.0019) H31(0.0967) H91A(-0.3048) H91B(-0.2863) H11A(-
 0.0937) H11B(-0.0718) H11C(-0.0269) H11D(-0.0498) H80A(-0.1926) H80B(-0.2177)
 H80C(-0.1976) H10E(-0.0178) H10F(-0.051) H82A(-0.1487) H82B(-0.1889) H82C(-
 0.1612) H81A(-0.1745) H81B(-0.1923) H81C(-0.1517) H11E(-0.0609) H11F(-0.0867)
 H10G(-0.114) H10H(-0.079) H10I(-0.094) H11G(-0.139) H11H(-0.1162) H11I(-
 0.1259) H84A(0.1371) H84B(0.1753) H84C(0.145) H10J(-0.0178) H10K(0.0151) H51A(-
 0.0184) H51B(0.0003) H51C(0.004) H10L(0.0744) H10M(0.0601) H11J(0.0719)
 H11K(0.0664) H78A(0.2148) H78B(0.2338) H78C(0.2087) H77A(0.1776) H77B(0.2013)
 H77C(0.1604) H10N(-0.0866) H10O(-0.0532) H72A(-0.1597) H72B(-0.1775) H72C(-
 0.1382) H86A(0.1809) H86B(0.1975) H86C(0.1596) H10P(0.0179) H10Q(0.0165)
 H10R(0.0439) H10S(0.0244) H10T(0.0879) H10U(0.1138) H10V(0.1067) H85A(0.1803)
 H85B(0.2102) H85C(0.1923) H11L(0.0606) H11M(0.095) H11N(0.0885) H74A(-0.1161)
 H74B(-0.1551) H74C(-0.1283) H76A(0.1702) H76B(0.2108) H76C(0.1902) H95A(0.025)
 H95B(0.0546) H95C(0.0537) H73A(-0.1704) H73B(-0.1948) H73C(-0.1802)
;
_shelx_hkl_checksum              87685
_shelx_res_checksum              92756
_shelxl_version_number           2013-3