A Route to a Cyclobutane-Linked Double-Looped System via a Helical Macrocycle
Klajn, Jan; Stawski, Wojciech; Chmielewski, Piotr Jan; Cybińska, Joanna; Pawlicki, Miłosz; Chemical Communications  (2019) –; doi:10.1039/C9CC01201J

data_7123181
_publ_section_title
;
 A Route to a Cyclobutane-Linked Double-Looped System via a Helical
 Macrocycle
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01201J
_journal_year                    2019
_chemical_formula_moiety         '2(C32 H33 N3), C H2 Cl2, C H1.57 Cl2'
_chemical_formula_sum            'C66 H70 Cl4 N6'
_chemical_formula_weight         1089.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-22 deposited with the CCDC.    2019-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.645(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9413(2)
_cell_length_b                   16.5587(3)
_cell_length_c                   31.2883(8)
_cell_measurement_reflns_used    12514
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4259
_cell_measurement_theta_min      2.7949
_cell_volume                     5604.2(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_details
;
  1 omega  -54.00   60.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0000  -79.0000    0.0000 153

  2 omega  -54.00   60.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0000  -79.0000   90.0000 153

  3 omega  -54.00   60.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0000  -79.0000  180.0000 153

  4 omega  -54.00   51.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       27.0000  -79.0000  270.0000 141
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0401383000
_diffrn_orient_matrix_UB_12      -0.0116436000
_diffrn_orient_matrix_UB_13      -0.0147149000
_diffrn_orient_matrix_UB_21      -0.0417624000
_diffrn_orient_matrix_UB_22      -0.0311293000
_diffrn_orient_matrix_UB_23      -0.0080824000
_diffrn_orient_matrix_UB_31      -0.0308028000
_diffrn_orient_matrix_UB_32      0.0270216000
_diffrn_orient_matrix_UB_33      -0.0156092000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            35275
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_min         2.801
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             2304
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     707
_refine_ls_number_reflns         11939
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0691
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1068P)^2^+5.7935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.2091
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8160
_reflns_number_total             11939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01201j9.cif
_cod_data_source_block           jk294
_cod_database_code               7123181
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 92.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.43
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H005(0.019) H006(0.02) H00L(0.021) H00S(0.023) H00T(0.022)
 H00U(0.023) H00W(0.022) H00X(0.022) H00Z(0.027) H010(0.022) H011(0.026)
 H013(0.028) H015(0.027) H016(0.027) H018(0.028) H01W(0.031) H01B(0.03)
 H01X(0.03) H01A(0.038) H01C(0.038) H01D(0.038) H01Y(0.038) H(0.038) HA(0.038)
 H01J(0.03) H01E(0.038) H01F(0.038) H01G(0.038) H01Z(0.032) H01O(0.031)
 H01(0.034) H0AA(0.04) HB(0.04) HC(0.04) H1AA(0.03) HD(0.03) H01H(0.042)
 H01I(0.042) H01K(0.042) H2AA(0.043) HE(0.043) HF(0.043) H01L(0.031)
 H01M(0.031) H01N(0.029) H01P(0.029) H3AA(0.031) HG(0.031) H01Q(0.048)
 H01R(0.048) H01S(0.048) H01T(0.05) H01U(0.05) H01V(0.05) H4AA(0.052) HH(0.052)
 HI(0.052) H02A(0.057) H02B(0.057) H02C(0.057) H02D(0.06) H02E(0.06) H02F(0.06)
 H02G(0.061) H02H(0.061) H02I(0.061) H1A(0.055) H1B(0.055) H2A(0.068) H2B(0.068)
 Fixed X: H005(0.299911) H006(0.705326) H00L(0.25295) H00S(0.534649)
 H00T(0.747957) H00U(0.926217) H00W(0.074039) H00X(0.469624) H00Z(0.65116)
 H010(0.020924) H011(0.984811) H013(0.972836) H015(0.356759) H016(0.036413)
 H018(0.693648) H01W(0.243957) H01B(0.766852) H01X(0.317651) H01A(0.286627)
 H01C(0.403426) H01D(0.367351) H01Y(0.62822) H(0.515938) HA(0.492947)
 H01J(0.308874) H01E(0.50441) H01F(0.485277) H01G(0.370476) H01Z(0.704816)
 H01O(0.117028) H01(0.896422) H0AA(0.636645) HB(0.600118) HC(0.716683)
 H1AA(0.624031) HD(0.496659) H01H(0.577119) H01I(0.610982) H01K(0.633612)
 H2AA(0.369817) HE(0.392191) HF(0.428235) H01L(0.515142) H01M(0.386676)
 H01N(0.499361) H01P(0.517668) H3AA(0.490453) HG(0.510985) H01Q(-0.217972)
 H01R(-0.224811) H01S(-0.159412) H01T(0.027787) H01U(-0.034931) H01V(0.09322)
 H4AA(1.163479) HH(1.232696) HI(1.220568) H02A(-0.004085) H02B(-0.132393) H02C(-
 0.120878) H02D(0.916676) H02E(1.046391) H02F(0.97924) H02G(1.126738)
 H02H(1.141759) H02I(1.012291) H1A(0.665342) H1B(0.662043) H2A(1.652234)
 H2B(1.655465)
 Fixed Y: H005(0.4116) H006(0.603136) H00L(0.376924) H00S(0.263355)
 H00T(0.641457) H00U(0.513186) H00W(0.502234) H00X(0.754331) H00Z(0.250757)
 H010(0.628102) H011(0.387672) H013(0.396802) H015(0.767703) H016(0.619776)
 H018(0.325344) H01W(0.765473) H01B(0.254038) H01X(0.693352) H01A(0.285496)
 H01C(0.283262) H01D(0.363311) H01Y(0.854811) H(0.856282) HA(0.847831)
 H01J(0.582301) H01E(0.171178) H01F(0.166979) H01G(0.167377) H01Z(0.433847)
 H01O(0.636803) H01(0.380652) H0AA(0.662734) HB(0.744989) HC(0.740084)
 H1AA(0.634946) HD(0.629054) H01H(0.37208) H01I(0.294174) H01K(0.297068)
 H2AA(0.72164) HE(0.727372) HF(0.648543) H01L(0.387367) H01M(0.380948)
 H01N(0.518269) H01P(0.511509) H3AA(0.504696) HG(0.497814) H01Q(0.592213)
 H01R(0.683046) H01S(0.659298) H01T(0.735354) H01U(0.753876) H01V(0.709751)
 H4AA(0.355895) HH(0.336984) HI(0.42642) H02A(0.603849) H02B(0.647592)
 H02C(0.556698) H02D(0.305166) H02E(0.262942) H02F(0.280842) H02G(0.463196)
 H02H(0.373021) H02I(0.415198) H1A(0.464305) H1B(0.375329) H2A(0.49136)
 H2B(0.508516)
 Fixed Z: H005(0.232025) H006(0.273904) H00L(0.068161) H00S(0.142012)
 H00T(0.437397) H00U(0.421749) H00W(0.085079) H00X(0.361742) H00Z(0.20652)
 H010(0.190926) H011(0.316605) H013(0.239819) H015(0.29727) H016(0.267345)
 H018(0.330106) H01W(0.2283) H01B(0.274798) H01X(0.173616) H01A(0.016114) H01C(-
 0.007387) H01D(0.014385) H01Y(0.439275) H(0.465043) HA(0.414567)
 H01J(0.367222) H01E(0.087048) H01F(0.036427) H01G(0.060973) H01Z(0.138925)
 H01O(0.34008) H01(0.166931) H0AA(0.491831) HB(0.511264) HC(0.487731)
 H1AA(0.178392) HD(0.148211) H01H(0.057025) H01I(0.032855) H01K(0.08351)
 H2AA(0.420495) HE(0.471081) HF(0.448183) H01L(0.356878) H01M(0.327399)
 H01N(0.352264) H01P(0.303776) H3AA(0.201169) HG(0.152892) H01Q(0.121057)
 H01R(0.106771) H01S(0.153119) H01T(0.137033) H01U(0.089644) H01V(0.097869)
 H4AA(0.354118) HH(0.400624) HI(0.384096) H02A(0.046772) H02B(0.042631)
 H02C(0.056676) H02D(0.411292) H02E(0.418167) H02F(0.371258) H02G(0.44951)
 H02H(0.46465) H02I(0.460804) H1A(-0.088567) H1B(-0.071699) H2A(0.422995)
 H2B(0.472408)
;
_shelx_res_checksum              36938
_olex2_submission_special_instructions 'No special instructions were received'