The effect of carboxylate position on the structure of a metal organic framework derived from cyclotriveratrylene
Martin, Adam D.; Easun, Timothy L.; Argent, Stephen P.; Lewis, William; Blake, Alexander J.; Schröder, Martin; CrystEngComm 19 (2017) 603–; doi:10.1039/C6CE01965J

data_7227122
_publ_section_title
;
 The effect of carboxylate position on the structure of a metal organic
 framework derived from cyclotriveratrylene
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              603
_journal_paper_doi               10.1039/C6CE01965J
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C184 H144 N O42 Zn6, 5(C4 H9 N O)'
_chemical_formula_sum            'C264 H331 N21 O62 Zn6'
_chemical_formula_weight         5182.70
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-03-23 deposited with the CCDC.
2016-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                68.750(5)
_cell_angle_beta                 88.214(4)
_cell_angle_gamma                60.764(6)
_cell_formula_units_Z            2
_cell_length_a                   23.7409(14)
_cell_length_b                   23.9301(14)
_cell_length_c                   31.1933(16)
_cell_measurement_reflns_used    17539
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.9920
_cell_measurement_theta_min      1.6450
_cell_volume                     14179.0(18)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -60.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000    0.0000    0.0000 175

  2 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000    0.0000 120

  3 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  120.0000 120

  4 omega  -60.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000  -50.0000  240.0000 120
;
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Kappa Rigaku Saturn724+'
_diffrn_measurement_method       'omega rotation'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_UB_11      0.0076638000
_diffrn_orient_matrix_UB_12      0.0257821000
_diffrn_orient_matrix_UB_13      -0.0053877000
_diffrn_orient_matrix_UB_21      -0.0101428000
_diffrn_orient_matrix_UB_22      0.0103572000
_diffrn_orient_matrix_UB_23      -0.0234213000
_diffrn_orient_matrix_UB_31      -0.0313195000
_diffrn_orient_matrix_UB_32      0.0228329000
_diffrn_orient_matrix_UB_33      0.0016050000
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  'Synchrotron '
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.1078
_diffrn_reflns_av_unetI/netI     0.1444
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            73911
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        20.148
_diffrn_reflns_theta_max         20.148
_diffrn_reflns_theta_min         1.537
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) 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    1.214
_exptl_crystal_description       block
_exptl_crystal_F_000             5476
_exptl_crystal_recrystallization_method 'Solvothermal Reaction'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.136
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.484
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2167
_refine_ls_number_reflns         29553
_refine_ls_number_restraints     3047
_refine_ls_restrained_S_all      1.436
_refine_ls_R_factor_all          0.2211
_refine_ls_R_factor_gt           0.1727
_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          0.4367
_refine_ls_wR_factor_ref         0.4728
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16964
_reflns_number_total             29553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce01965j2.cif
_cod_data_source_block           2-Zn
_cod_depositor_comments
'Adding full bibliography for 7227120--7227122.cif.'
_cod_original_cell_volume        14179.1(16)
_cod_database_code               7227122
_nottingham_internal_coll_number 12315
_nottingham_internal_coll_client ADM/MS
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time 1.0
_nottingham_internal_coll_frame_width 1.0
_nottingham_internal_coll_user   ADM
_nottingham_internal_coll_date   23/07/2013
_nottingham_internal_coll_location DLS
_nottingham_internal_process_date 23/07/2013
_nottingham_internal_process_user ADM
_nottingham_internal_solution_date 23/07/2013
_nottingham_internal_solution_user ADM
_nottingham_internal_refinement_date 05/01/2016
_nottingham_internal_refinement_user ADM/pczspa
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_platon_squeeze_void_probe_radius 1.20
_chemical_oxdiff_formula         'C45 H36 O9 Zn3'
_reflns_odcompleteness_completeness 96.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.50
_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, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O41-H41
 0.84 with sigma of 0.005
 H37A-H37B
 1.37 with sigma of 0.02
 O37-H37A = O37-H37B
 0.84 with sigma of 0.005
 H37A-O1A
 2 with sigma of 0.05
 O1D-H41
 1.62 with sigma of 0.05
 O1A-C2A
 1.23 with sigma of 0.005
 C2A-C3A
 1.5 with sigma of 0.005
 C2A-N4A
 1.3 with sigma of 0.005
 N4A-C5A
 1.46 with sigma of 0.005
 N4A-C6A
 1.46 with sigma of 0.005
 O1A-N4A
 2.23 with sigma of 0.02
 C3A-N4A
 2.42 with sigma of 0.02
 C2A-C5A
 2.43 with sigma of 0.02
 C2A-C6A
 2.45 with sigma of 0.02
 C5A-C6A
 2.5 with sigma of 0.02
 O1B-C2B
 1.23 with sigma of 0.005
 C2B-C3B
 1.5 with sigma of 0.005
 C2B-N4B
 1.3 with sigma of 0.005
 N4B-C5B
 1.46 with sigma of 0.005
 N4B-C6B
 1.46 with sigma of 0.005
 O1B-N4B
 2.23 with sigma of 0.02
 C3B-N4B
 2.42 with sigma of 0.02
 C2B-C5B
 2.43 with sigma of 0.02
 C2B-C6B
 2.45 with sigma of 0.02
 C5B-C6B
 2.5 with sigma of 0.02
 O1C-C2C
 1.23 with sigma of 0.005
 C2C-C3C
 1.5 with sigma of 0.005
 C2C-N4C
 1.3 with sigma of 0.005
 N4C-C5C
 1.46 with sigma of 0.005
 N4C-C6C
 1.46 with sigma of 0.005
 O1C-N4C
 2.23 with sigma of 0.02
 C3C-N4C
 2.42 with sigma of 0.02
 C2C-C5C
 2.43 with sigma of 0.02
 C2C-C6C
 2.45 with sigma of 0.02
 C5C-C6C
 2.5 with sigma of 0.02
 O1D-C2D
 1.23 with sigma of 0.005
 C2D-C3D
 1.5 with sigma of 0.005
 C2D-N4D
 1.3 with sigma of 0.005
 N4D-C5D
 1.46 with sigma of 0.005
 N4D-C6D
 1.46 with sigma of 0.005
 O1D-N4D
 2.23 with sigma of 0.02
 C3D-N4D
 2.42 with sigma of 0.02
 C2D-C5D
 2.43 with sigma of 0.02
 C2D-C6D
 2.45 with sigma of 0.02
 C5D-C6D
 2.5 with sigma of 0.02
 O1E-C2E
 1.23 with sigma of 0.005
 C2E-C3E
 1.5 with sigma of 0.005
 C2E-N4E
 1.3 with sigma of 0.005
 N4E-C5E
 1.46 with sigma of 0.005
 N4E-C6E
 1.46 with sigma of 0.005
 O1E-N4E
 2.23 with sigma of 0.02
 C3E-N4E
 2.42 with sigma of 0.02
 C2E-C5E
 2.43 with sigma of 0.02
 C2E-C6E
 2.45 with sigma of 0.02
 C5E-C6E
 2.5 with sigma of 0.02
 O1F-C2F
 1.23 with sigma of 0.005
 C2F-C3F
 1.5 with sigma of 0.005
 C2F-N4F
 1.3 with sigma of 0.005
 N4F-C5F
 1.46 with sigma of 0.005
 N4F-C6F
 1.46 with sigma of 0.005
 O1F-N4F
 2.23 with sigma of 0.02
 C3F-N4F
 2.42 with sigma of 0.02
 C2F-C5F
 2.43 with sigma of 0.02
 C2F-C6F
 2.45 with sigma of 0.02
 C5F-C6F
 2.5 with sigma of 0.02
 O16-C83 \\sim O10-C59 \\sim O13-C71 \\sim O4-C26 \\sim O7-C38 \\sim O1-C14
\\sim O28-C149 \\sim O34-C173
 \\sim O31-C161 \\sim O19-C104 \\sim O22-C116 \\sim O25-C128
 with sigma of 0.02
 O28-C147 \\sim O34-C171 \\sim O31-C159 \\sim O22-C113 \\sim O25-C125 \\sim
O19-C101 \\sim O10-C57 ~
 O16-C81 \\sim O13-C69 \\sim O4-C23 \\sim O1-C11 \\sim O7-C35
 with sigma of 0.02
 C156-C152 \\sim C168-C164 \\sim C180-C176 \\sim C111-C109 \\sim C135-C133
\\sim C123-C121 \\sim C78-
 C74 \\sim C66-C62 \\sim C90-C86 \\sim C21-C19 \\sim C45-C43
 with sigma of 0.02
 C138-C137 \\sim C139-C138 \\sim C144-C136 \\sim C144-C143 \\sim C142-C141
\\sim C141-C140 \\sim C93-
 C92 \\sim C94-C93 \\sim C99-C91 \\sim C99-C98 \\sim C96-C95 \\sim C97-C96
\\sim C49-C48 \\sim C48-C47 ~
 C54-C46 \\sim C54-C53 \\sim C52-C51 \\sim C51-C50 \\sim C9-C8 \\sim C8-C7
\\sim C6-C5 \\sim C5-C4 \\sim C3-C2
 \\sim C2-C1
 with sigma of 0.02
 C173-C171 \\sim C149-C147
 with sigma of 0.02
 C147-C149 \\sim C171-C173 \\sim C159-C161 \\sim C113-C116 \\sim C125-C128
\\sim C101-C104 \\sim C35-
 C38 \\sim C11-C14 \\sim C23-C26 \\sim C57-C59 \\sim C69-C71 \\sim C81-C83
 with sigma of 0.02
 C46-C53 \\sim C52-C50 \\sim C49-C47 \\sim C7-C9 \\sim C1-C3 \\sim C4-C6 \\sim
C98-C91 \\sim C92-C94 \\sim C95-
 C97 \\sim C137-C139 \\sim C140-C142 \\sim C143-C136
 with sigma of 0.02
 Zn1-O37 \\sim Zn4-O42 \\sim Zn3-O41 \\sim Zn6-O44 \\sim Zn5-O43
 with sigma of 0.02
3. Restrained planarity
 O5, O6, C28, C31, C33
 with sigma of 0.1
 O8, O9, C40, C43, C45
 with sigma of 0.1
 O2, O3, C16, C19, C21
 with sigma of 0.1
 O17, O18, C86, C89, C90
 with sigma of 0.1
 O11, O12, C62, C65, C66
 with sigma of 0.1
 O14, O15, C74, C77, C78
 with sigma of 0.1
 O29, O30, C152, C155, C156
 with sigma of 0.1
 O32, O33, C164, C167, C168
 with sigma of 0.1
 O35, O36, C176, C179, C180
 with sigma of 0.1
 O26, O27, C130, C133, C135
 with sigma of 0.1
 O20, O21, C106, C109, C111
 with sigma of 0.1
 O23, O24, C118, C121, C123
 with sigma of 0.1
 O1A, C2A, C3A, N4A, C5A, C6A
 with sigma of 0.1
 O1B, C2B, C3B, N4B, C5B, C6B
 with sigma of 0.1
 O1C, C2C, C3C, N4C, C5C, C6C
 with sigma of 0.1
 O1D, C2D, C3D, N4D, C5D, C6D
 with sigma of 0.1
 O1E, C2E, C3E, N4E, C5E, C6E
 with sigma of 0.1
 O1F, C2F, C3F, N4F, C5F, C6F
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C26 \\sim O34 \\sim C40 \\sim C41 \\sim C59 \\sim C71 \\sim C119: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08
O1A \\sim C2A \\sim C3A \\sim N4A \\sim C5A \\sim C6A \\sim O1B \\sim C2B \\sim
C3B \\sim N4B \\sim C5B \\sim C6B \\sim O1C \\sim C2C \\sim C3C \\sim N4C \\sim
C5C \\sim C6C \\sim O1D \\sim C2D \\sim C3D \\sim N4D \\sim C5D \\sim C6D \\sim
O1E \\sim C2E \\sim C3E \\sim N4E \\sim C5E \\sim C6E \\sim O1F \\sim C2F \\sim
C3F \\sim N4F \\sim C5F \\sim C6F: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04
Uanis(C104) \\sim Ueq, Uanis(C128) \\sim Ueq, Uanis(C116) \\sim Ueq,
Uanis(C173) \\sim Ueq, Uanis(C149) \\sim Ueq, Uanis(C161) \\sim Ueq, Uanis(C59)
\\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C83) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C38) \\sim Ueq, Uanis(C26) \\sim Ueq: with sigma of 0.004 and sigma for
terminal atoms of 0.008
Uanis(C17) \\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C89)
\\sim Ueq, Uanis(C119) \\sim Ueq: with sigma of 0.008 and sigma for terminal
atoms of 0.016
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Same fragment restrains
{O1D, C2D, C3D, N4D, C5D, C6D} sigma for 1-2: 0.01, 1-3: 0.02
as
{O1A, C2A, C3A, N4A, C5A, C6A}
{O1D, C2D, C3D, N4D, C5D, C6D} sigma for 1-2: 0.01, 1-3: 0.02
as
{O1B, C2B, C3B, N4B, C5B, C6B}
{O1D, C2D, C3D, N4D, C5D, C6D} sigma for 1-2: 0.01, 1-3: 0.02
as
{O1C, C2C, C3C, N4C, C5C, C6C}
{O1D, C2D, C3D, N4D, C5D, C6D} sigma for 1-2: 0.01, 1-3: 0.02
as
{O1E, C2E, C3E, N4E, C5E, C6E}
{O1D, C2D, C3D, N4D, C5D, C6D} sigma for 1-2: 0.01, 1-3: 0.02
as
{O1F, C2F, C3F, N4F, C5F, C6F}
7. Others
 Uiso(O1A)=Uiso(C2A)=Uiso(C3A)=Uiso(N4A)=Uiso(C5A)=Uiso(C6A)=FVAR(1)
 Uiso(O1B)=Uiso(C2B)=Uiso(C3B)=Uiso(N4B)=Uiso(C5B)=Uiso(C6B)=FVAR(2)
 Uiso(O1C)=Uiso(C2C)=Uiso(C3C)=Uiso(N4C)=Uiso(C5C)=Uiso(C6C)=FVAR(3)
 Uiso(O1D)=Uiso(C2D)=Uiso(C3D)=Uiso(N4D)=Uiso(C5D)=Uiso(C6D)=FVAR(4)
 Uiso(O1E)=Uiso(C2E)=Uiso(C3E)=Uiso(N4E)=Uiso(C5E)=Uiso(C6E)=FVAR(5)
 Uiso(O1F)=Uiso(C2F)=Uiso(C3F)=Uiso(N4F)=Uiso(C5F)=Uiso(C6F)=FVAR(6)
8.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C8(H8A,H8B), C48(H48A,H48B), C51(H51A,H51B),
 C54(H54A,H54B), C93(H93A,H93B), C96(H96A,H96B), C99(H99A,H99B), C138(H13A,
 H13B), C141(H14D,H14E), C144(H14F,H14G)
8.b Me refined with riding coordinates:
 C14(H14A,H14B,H14C), C26(H26A,H26B,H26C), C38(H38A,H38B,H38C), C59(H59A,H59B,
 H59C), C71(H71A,H71B,H71C), C83(H83A,H83B,H83C), C104(H10A,H10B,H10C),
 C116(H11A,H11B,H11C), C128(H12A,H12B,H12C), C149(H14H,H14I,H14J), C161(H16A,
 H16B,H16C), C173(H17A,H17B,H17C), C3A(H3AA,H3AB,H3AC), C5A(H5AA,H5AB,H5AC),
 C6A(H6AA,H6AB,H6AC), C3B(H3BA,H3BB,H3BC), C5B(H5BA,H5BB,H5BC), C6B(H6BA,H6BB,
 H6BC), C3C(H3CA,H3CB,H3CC), C5C(H5CA,H5CB,H5CC), C6C(H6CA,H6CB,H6CC), C3D(H3DA,
 H3DB,H3DC), C5D(H5DA,H5DB,H5DC), C6D(H6DA,H6DB,H6DC), C3E(H3EA,H3EB,H3EC),
 C5E(H5EA,H5EB,H5EC), C6E(H6EA,H6EB,H6EC), C3F(H3FA,H3FB,H3FC), C5F(H5FA,H5FB,
 H5FC), C6F(H6FA,H6FB,H6FC)
8.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C16(H16), C17(H17), C18(H18), C20(H20), C22(H22),
 C25(H25), C28(H28), C29(H29), C30(H30), C32(H32), C34(H34), C37(H37), C40(H40),
  C41(H41A), C42(H42), C44(H44), C55(H55), C58(H58), C61(H61), C63(H63),
 C64(H64), C65(H65), C67(H67), C70(H70), C73(H73), C75(H75), C76(H76), C77(H77),
  C79(H79), C82(H82), C85(H85), C87(H87), C88(H88), C89(H89), C100(H100),
 C103(H103), C106(H106), C107(H107), C108(H108), C110(H110), C112(H112),
 C115(H115), C118(H118), C119(H119), C120(H120), C122(H122), C124(H124),
 C127(H127), C130(H130), C131(H131), C132(H132), C134(H134), C145(H145),
 C148(H148), C151(H151), C153(H153), C154(H154), C155(H155), C157(H157),
 C160(H160), C163(H163), C165(H165), C166(H166), C167(H167), C169(H169),
 C172(H172), C175(H175), C177(H177), C178(H178), C179(H179)
;
_shelx_res_checksum              16668
_shelx_fab_checksum              80588
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'