A 2,3-dialkoxynaphthalene-based naphthocage.
Lu, Song-Bo; Chai, Hongxin; Ward, Jas S.; Quan, Mao; Zhang, Jin; Rissanen, Kari; Luo, Ray; Yang, Liu-Pan; Jiang, Wei; Chemical communications (Cambridge, England) 56 (2020) 888–891; doi:10.1039/c9cc09585c

data_7125654
_publ_section_title
;
 A 2,3-dialkoxynaphthalene-based naphthocage.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              888
_journal_page_last               891
_journal_paper_doi               10.1039/c9cc09585c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C84 H108 O12, C8 H20 N, F6 P'
_chemical_formula_sum            'C92 H128 F6 N O12 P'
_chemical_formula_weight         1584.92
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-10 deposited with the CCDC.	2019-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.796(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7124(6)
_cell_length_b                   35.8329(17)
_cell_length_c                   16.5563(7)
_cell_measurement_reflns_used    5827
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      69.3000
_cell_measurement_theta_min      2.6360
_cell_volume                     9320.6(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -116.00 -19.00   1.00   14.00    --  -41.90 -37.00 -30.00   97
  2  \w      1.00  83.00   1.00   14.00    --   41.90 -99.00 120.00   82
  3  \w     51.00  96.00   1.00   14.00    --   41.90-125.00  60.00   45
  4  \w      9.00 118.00   1.00   14.00    --   41.90  77.00-120.00  109
  5  \w     35.00 139.00   1.00   50.00    --  110.86 -30.00 -90.00  104
  6  \w     86.00 175.00   1.00   50.00    --  110.86  45.00  90.00   89
  7  \w     28.00 109.00   1.00   50.00    --  110.86 -94.00 120.00   81
  8  \w     38.00 122.00   1.00   50.00    --  110.86-125.00 -30.00   84
  9  \w     41.00 133.00   1.00   50.00    --  110.86 -61.00 150.00   92
 10  \w     37.00  99.00   1.00   50.00    --  110.86 -30.00  60.00   62
 11  \w     43.00 155.00   1.00   50.00    --  110.86 -15.00  90.00  112
 12  \w     49.00 143.00   1.00   50.00    --  110.86 -77.00 -60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0932731000
_diffrn_orient_matrix_UB_12      -0.0000977000
_diffrn_orient_matrix_UB_13      -0.0299325000
_diffrn_orient_matrix_UB_21      0.0023382000
_diffrn_orient_matrix_UB_22      0.0428203000
_diffrn_orient_matrix_UB_23      -0.0078165000
_diffrn_orient_matrix_UB_31      0.0301677000
_diffrn_orient_matrix_UB_32      -0.0037182000
_diffrn_orient_matrix_UB_33      -0.0877908000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            58798
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.502
_diffrn_reflns_theta_min         2.940
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.817
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       plate
_exptl_crystal_F_000             3408
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.111
_exptl_crystal_size_min          0.038
_refine_diff_density_max         1.034
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.673
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1244
_refine_ls_number_reflns         18892
_refine_ls_number_restraints     685
_refine_ls_restrained_S_all      1.673
_refine_ls_R_factor_all          0.2178
_refine_ls_R_factor_gt           0.1760
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4702
_refine_ls_wR_factor_ref         0.4931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11598
_reflns_number_total             18892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09585c2.cif
_cod_data_source_block           4-PF6@2
_cod_depositor_comments          'Adding full bibliography for 7125654.cif.'
_cod_database_code               7125654
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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. Restrained distances
 C41A-C40A
 1.55 with sigma of 0.02
 O62-C53
 1.45 with sigma of 0.01
 C88-C87 = C88A-C87A = C89A-C88A = C89-C88
 1.55 with sigma of 0.02
 O86-C87 = O86-C87A
 1.45 with sigma of 0.02
 C91A-C92A
 1.5 with sigma of 0.02
 O90A-C91A
 1.45 with sigma of 0.01
 C91-C92
 1.55 with sigma of 0.02
 C92-C93
 1.55 with sigma of 0.02
 O90A-C78
 1.45 with sigma of 0.01
 O90-C78
 1.45 with sigma of 0.01
 C93A-C92A
 1.55 with sigma of 0.02
 C54-O66A
 1.45 with sigma of 0.01
 O66-C67
 1.45 with sigma of 0.02
 C67A-C68A
 1.55 with sigma of 0.02
 C69-C68
 1.55 with sigma of 0.02
 O66-C54
 1.45 with sigma of 0.01
 O66A-C67A
 1.45 with sigma of 0.02
 C67-C68
 1.55 with sigma of 0.02
 C65A-C64A
 1.55 with sigma of 0.02
 O62A-C53
 1.45 with sigma of 0.02
 O62A-H65A
 2 with sigma of 0.02
 C8-C19
 1.55 with sigma of 0.02
 C21A-C10
 1.55 with sigma of 0.02
 H19C-H48B
 -1.9 with sigma of 0.01
 H94B-H91D
 -1.9 with sigma of 0.01
 H72C-H19D
 -1.9 with sigma of 0.01
 C87A-C89A
 2.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O42 \\sim C43 \\sim C43A \\sim C44 \\sim C44A \\sim C45 \\sim C45A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
O38 \\sim C39A \\sim C39 \\sim C40A \\sim C40 \\sim C41A \\sim C41: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
O86 \\sim C87 \\sim C87A \\sim C88 \\sim C88A \\sim C89 \\sim C89A: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04
C78 \\sim O90 \\sim O90A \\sim C91 \\sim C91A \\sim C92 \\sim C92A \\sim C93
\\sim C93A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C54 \\sim O66 \\sim O66A \\sim C67 \\sim C67A \\sim C68 \\sim C68A \\sim C69
\\sim C69A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C53 \\sim O62A \\sim O62 \\sim C63A \\sim C63 \\sim C64A \\sim C64 \\sim C65A
\\sim C65: within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
C8 \\sim C19 \\sim C19A \\sim C20 \\sim C20A: within 1.7A with sigma of 0.02
and sigma for terminal atoms of 0.04
Uanis(C21) = Uanis(C21A)
4. Rigid body (RIGU) restrains
 C56, C57, C58, C59, C60, C61
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 P111, F112, F113, F114, F115, F116, F117
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10, C21A, C21, C22A, C22
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C9, O71, C72, C72A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(C43A)=Sof(H43C)=Sof(H43D)=Sof(C44A)=Sof(H44C)=Sof(H44D)=Sof(C45A)=
 Sof(H45D)=Sof(H45E)=Sof(H45F)=1-FVAR(1)
 Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C45)=Sof(H45A)=
 Sof(H45B)=Sof(H45C)=FVAR(1)
 Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=
 Sof(C21)=Sof(H21C)=Sof(H21D)=Sof(C22)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C72A)=
 Sof(H72C)=Sof(H72D)=1-FVAR(2)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21A)=
 Sof(H21A)=Sof(H21B)=Sof(C22A)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C72)=Sof(H72A)=
 Sof(H72B)=FVAR(2)
 Sof(C39)=Sof(H39C)=Sof(H39D)=Sof(C40)=Sof(H40C)=Sof(H40D)=Sof(C41)=Sof(H41D)=
 Sof(H41E)=Sof(H41F)=1-FVAR(3)
 Sof(C39A)=Sof(H39A)=Sof(H39B)=Sof(C40A)=Sof(H40A)=Sof(H40B)=Sof(C41A)=
 Sof(H41A)=Sof(H41B)=Sof(H41C)=FVAR(3)
 Sof(O62A)=Sof(C63A)=Sof(H63A)=Sof(H63B)=Sof(C64A)=Sof(H64A)=Sof(H64B)=
 Sof(C65A)=Sof(H65A)=Sof(H65B)=Sof(H65C)=1-FVAR(4)
 Sof(O62)=Sof(C63)=Sof(H63C)=Sof(H63D)=Sof(C64)=Sof(H64C)=Sof(H64D)=Sof(C65)=
 Sof(H65D)=Sof(H65E)=Sof(H65F)=FVAR(4)
 Sof(C87A)=Sof(H87C)=Sof(H87D)=Sof(C88A)=Sof(H88C)=Sof(H88D)=Sof(C89A)=
 Sof(H89D)=Sof(H89E)=Sof(H89F)=1-FVAR(5)
 Sof(C87)=Sof(H87A)=Sof(H87B)=Sof(C88)=Sof(H88A)=Sof(H88B)=Sof(C89)=Sof(H89A)=
 Sof(H89B)=Sof(H89C)=FVAR(5)
 Sof(O90A)=Sof(C91A)=Sof(H91C)=Sof(H91D)=Sof(C92A)=Sof(H92C)=Sof(H92D)=
 Sof(C93A)=Sof(H93D)=Sof(H93E)=Sof(H93F)=1-FVAR(6)
 Sof(O90)=Sof(C91)=Sof(H91A)=Sof(H91B)=Sof(C92)=Sof(H92A)=Sof(H92B)=Sof(C93)=
 Sof(H93A)=Sof(H93B)=Sof(H93C)=FVAR(6)
 Sof(O66A)=Sof(C67A)=Sof(H67C)=Sof(H67D)=Sof(C68A)=Sof(H68C)=Sof(H68D)=
 Sof(C69A)=Sof(H69D)=Sof(H69E)=Sof(H69F)=1-FVAR(7)
 Sof(O66)=Sof(C67)=Sof(H67A)=Sof(H67B)=Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(C69)=
 Sof(H69A)=Sof(H69B)=Sof(H69C)=FVAR(7)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C17(H17A,H17B), C19(H19A,H19B), C19A(H19C,
 H19D), C21A(H21A,H21B), C21(H21C,H21D), C23(H23A,H23B), C25(H25A,H25B),
 C27(H27A,H27B), C39A(H39A,H39B), C39(H39C,H39D), C40A(H40A,H40B), C40(H40C,
 H40D), C43(H43A,H43B), C43A(H43C,H43D), C44(H44A,H44B), C44A(H44C,H44D),
 C46(H46A,H46B), C48(H48A,H48B), C49(H49A,H49B), C51(H51A,H51B), C63A(H63A,
 H63B), C63(H63C,H63D), C64A(H64A,H64B), C64(H64C,H64D), C67(H67A,H67B),
 C67A(H67C,H67D), C68(H68A,H68B), C68A(H68C,H68D), C70(H70A,H70B), C72(H72A,
 H72B), C72A(H72C,H72D), C73(H73A,H73B), C75(H75A,H75B), C87(H87A,H87B),
 C87A(H87C,H87D), C88(H88A,H88B), C88A(H88C,H88D), C91(H91A,H91B), C91A(H91C,
 H91D), C92(H92A,H92B), C92A(H92C,H92D), C94(H94A,H94B), C96(H96A,H96B),
 C102(H10A,H10B), C104(H10F,H10G), C106(H10K,H10L), C108(H10P,H10Q)
6.b Aromatic/amide H refined with riding coordinates:
 C33(H33), C34(H34), C35(H35), C36(H36), C59(H59), C58(H58), C57(H57),
 C60(H60), C84(H84), C83(H83), C82(H82), C81(H81)
6.c Fitted hexagon refined as free rotating group:
 C59(C58,C57,C56,C61,C60), C85(C84,C83,C82,C81,C80)
6.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C), C20A(H20D,H20E,H20F), C22A(H22A,H22B,H22C), C22(H22D,H22E,H22F),
 C24(H24A,H24B,H24C), C41A(H41A,H41B,H41C), C41(H41D,H41E,H41F), C45(H45A,H45B,
 H45C), C45A(H45D,H45E,H45F), C65A(H65A,H65B,H65C), C65(H65D,H65E,H65F),
 C69(H69A,H69B,H69C), C69A(H69D,H69E,H69F), C89(H89A,H89B,H89C), C89A(H89D,H89E,
 H89F), C93(H93A,H93B,H93C), C93A(H93D,H93E,H93F), C103(H10C,H10D,H10E),
 C105(H10H,H10I,H10J), C107(H10M,H10N,H10O), C109(H10R,H10S,H10T)
;
_shelx_res_checksum              68141
_shelx_fab_checksum              93697
_ins_header
;
TITL OHD039-G2@2,3-NC_2_scale in P2(1)/m 
REM P2(1)/m (#11 in standard setting)
CELL 1.54184  15.712445  35.832881  16.556293  90.0000  90.7959  90.0000
ZERR    4.00   0.000614   0.001715   0.000662   0.0000   0.0035   0.0000
LATT  1
SYMM -x, y+1/2,-z 
SFAC C H N O F P
UNIT 368.00 512.00 4.00 48.00 24.00 4.00
TREF
HKLF 4
END
;
_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 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.820