#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:43:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180516 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/85/7218580.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7218580
loop_
_publ_author_name
'Forgan, Ross S.'
'Marshall, Ross J.'
'Struckmann, Mona'
'Bleine, Aurore B.'
'Long, De-Liang'
'Bernini, María C.'
'Fairen-Jimenez, David'
_publ_section_title
;
 Structure-directing factors when introducing hydrogen bond functionality
 to metal--organic frameworks
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              299
_journal_paper_doi               10.1039/C4CE01379D
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C25 H18 N4 O5 Zn, 4(C3 H7 N O)'
_chemical_formula_sum            'C37 H46 N8 O9 Zn'
_chemical_formula_weight         812.19
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.25(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.381(3)
_cell_length_b                   14.170(3)
_cell_length_c                   19.415(4)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.0
_cell_measurement_theta_min      2.36
_cell_volume                     4367.9(16)
_computing_cell_refinement       Apex2
_computing_data_collection       Apex2
_computing_data_reduction        Apex2
_computing_molecular_graphics    Diamond3
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2008 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Apex II Quazar CCD'
_diffrn_measurement_method       'ω & π scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            70868
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.764
_diffrn_reflns_theta_min         1.926
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.465
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   TWINABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1704
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_refine_diff_density_max         1.18
_refine_diff_density_min         -1.08
_refine_diff_density_rms         0.15
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     402
_refine_ls_number_reflns         8546
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0905
_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/[σ²(Fo²)+(0.1650P)²+11.2315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2450
_refine_ls_wR_factor_ref         0.2956
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6111
_reflns_number_total             8546
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce01379d2.cif
_cod_data_source_block           rsfms1069b
_cod_depositor_comments
'Adding full bibliography for 7218580--7218583.cif.'
_cod_database_code               7218580
#BEGIN Tags that were not found in dictionaries:
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.941
_shelx_estimated_absorpt_t_max   0.976
_exptl_absorpt_special_details   none
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Zn1 Zn 0.76895(6) 0.56837(6) 0.67839(4) 0.0362(3) Uani 1 1 d . . .
O1 O 0.7004(4) 0.6385(4) 0.7271(3) 0.0451(13) Uani 1 1 d . . .
O2 O 0.8126(5) 0.6986(6) 0.8053(4) 0.070(2) Uani 1 1 d . . .
O3 O 0.7751(6) 0.6905(6) 0.5823(5) 0.083(3) Uani 1 1 d . . .
O4 O 0.8633(5) 0.5780(6) 0.6340(4) 0.079(2) Uani 1 1 d . . .
O5 O 1.0280(4) 0.2245(5) 0.9029(3) 0.0569(18) Uani 1 1 d . . .
O6 O 0.9322(8) 0.9053(8) 0.7035(6) 0.080(3) Uiso 0.7 1 d D . P
O7 O 0.7652(16) 0.3759(17) 0.2273(12) 0.137(9) Uiso 0.5 1 d D . P
O8 O 0.2354(9) 0.4538(10) 0.5809(7) 0.044(3) Uiso 0.4 1 d D . P
O9 O 1.140(3) 0.438(3) 0.901(2) 0.084(12) Uiso 0.2 1 d D . P
N1 N 0.8178(5) 0.4679(5) 0.7549(3) 0.0441(16) Uani 1 1 d . . .
N2 N 0.6717(4) 0.5013(5) 0.6102(3) 0.0438(17) Uani 1 1 d . . .
N3 N 0.8935(5) 0.2618(5) 0.9101(3) 0.0439(17) Uani 1 1 d . . .
H3 H 0.8550 0.2470 0.9328 0.053 Uiso 1 1 calc R U .
N4 N 0.4754(5) 0.3371(5) 0.4925(3) 0.0481(18) Uani 1 1 d . . .
H4 H 0.4303 0.3367 0.5095 0.058 Uiso 1 1 calc R U .
N5 N 1.0013(6) 0.7679(7) 0.7332(6) 0.050(3) Uani 0.7 1 d D . P
N6 N 0.6654(10) 0.3931(11) 0.2866(8) 0.058(4) Uiso 0.5 1 d D . P
N7 N 0.1675(10) 0.4230(11) 0.6665(8) 0.041(4) Uiso 0.4 1 d D . P
N8 N 1.065(3) 0.449(3) 0.987(2) 0.071(12) Uiso 0.2 1 d D . P
C1 C 0.7378(6) 0.6817(6) 0.7857(4) 0.044(2) Uani 1 1 d . . .
C2 C 0.6786(6) 0.7113(6) 0.8307(4) 0.044(2) Uani 1 1 d . . .
C3 C 0.7063(7) 0.7698(7) 0.8877(5) 0.060(3) Uani 1 1 d . . .
H3A H 0.7620 0.7942 0.8980 0.073 Uiso 1 1 calc R U .
C4 C 0.6526(7) 0.7937(8) 0.9305(5) 0.063(3) Uani 1 1 d . . .
H4A H 0.6721 0.8348 0.9697 0.076 Uiso 1 1 calc R U .
C5 C 0.5721(7) 0.7589(7) 0.9172(5) 0.053(2) Uani 1 1 d . . .
C6 C 0.5448(7) 0.7058(9) 0.8575(6) 0.071(3) Uani 1 1 d . . .
H6 H 0.4878 0.6854 0.8449 0.086 Uiso 1 1 calc R U .
C7 C 0.5975(7) 0.6806(9) 0.8144(5) 0.073(3) Uani 1 1 d . . .
H7 H 0.5769 0.6421 0.7738 0.088 Uiso 1 1 calc R U .
C8 C 0.5143(6) 0.7835(7) 0.9623(5) 0.052(2) Uani 1 1 d . . .
C9 C 0.5255(9) 0.8659(10) 1.0011(8) 0.100(5) Uani 1 1 d . . .
H9 H 0.5708 0.9075 1.0005 0.120 Uiso 1 1 calc R U .
C10 C 0.4493(9) 0.7275(7) 0.9649(7) 0.088(5) Uani 1 1 d . . .
H10 H 0.4409 0.6711 0.9376 0.106 Uiso 1 1 calc R U .
C11 C 0.4668(8) 0.8859(12) 1.0419(8) 0.105(5) Uani 1 1 d . . .
H11 H 0.4724 0.9438 1.0672 0.127 Uiso 1 1 calc R U .
C12 C 0.4048(7) 0.8290(7) 1.0468(5) 0.058(3) Uani 1 1 d . . .
C13 C 0.3932(9) 0.7494(8) 1.0068(7) 0.085(4) Uani 1 1 d . . .
H13 H 0.3473 0.7086 1.0072 0.101 Uiso 1 1 calc R U .
C14 C 0.8431(7) 0.6464(8) 0.5900(5) 0.060(3) Uani 1 1 d . . .
C15 C 0.8927(6) 0.4303(6) 0.7654(4) 0.0410(19) Uani 1 1 d . . .
H15 H 0.9278 0.4509 0.7361 0.049 Uiso 1 1 calc R U .
C16 C 0.9248(6) 0.3622(6) 0.8165(4) 0.046(2) Uani 1 1 d . . .
H16 H 0.9811 0.3402 0.8236 0.056 Uiso 1 1 calc R U .
C17 C 0.8726(5) 0.3277(6) 0.8564(4) 0.0418(19) Uani 1 1 d . . .
C18 C 0.7916(6) 0.3662(7) 0.8448(5) 0.055(2) Uani 1 1 d . . .
H18 H 0.7539 0.3454 0.8718 0.066 Uiso 1 1 calc R U .
C19 C 0.7677(6) 0.4344(6) 0.7937(5) 0.049(2) Uani 1 1 d . . .
H19 H 0.7123 0.4592 0.7856 0.059 Uiso 1 1 calc R U .
C20 C 0.9712(6) 0.2170(6) 0.9309(4) 0.0431(19) Uani 1 1 d . . .
C21 C 0.6034(6) 0.4783(7) 0.6331(4) 0.046(2) Uani 1 1 d . . .
H21 H 0.6004 0.4999 0.6788 0.055 Uiso 1 1 calc R U .
C22 C 0.5375(6) 0.4253(6) 0.5946(4) 0.045(2) Uani 1 1 d . . .
H22 H 0.4898 0.4130 0.6129 0.054 Uiso 1 1 calc R U .
C23 C 0.5411(5) 0.3896(6) 0.5285(4) 0.0384(18) Uani 1 1 d . . .
C24 C 0.6112(5) 0.4163(6) 0.5038(4) 0.0409(19) Uani 1 1 d . . .
H24 H 0.6150 0.3977 0.4577 0.049 Uiso 1 1 calc R U .
C25 C 0.6738(5) 0.4687(6) 0.5454(4) 0.0381(17) Uani 1 1 d . . .
H25 H 0.7216 0.4832 0.5278 0.046 Uiso 1 1 calc R U .
C26 C 0.9361(8) 0.8281(8) 0.7279(7) 0.051(3) Uiso 0.7 1 d D . P
H26 H 0.8897 0.8071 0.7451 0.061 Uiso 0.7 1 calc R U P
C27 C 1.0030(10) 0.6812(10) 0.7734(8) 0.067(4) Uiso 0.7 1 d D . P
H27A H 1.0538 0.6452 0.7723 0.100 Uiso 0.7 1 calc R U P
H27B H 1.0034 0.6965 0.8227 0.100 Uiso 0.7 1 calc R U P
H27C H 0.9530 0.6435 0.7522 0.100 Uiso 0.7 1 calc R U P
C28 C 1.0675(13) 0.7922(15) 0.6961(11) 0.100(6) Uiso 0.7 1 d D . P
H28A H 1.1105 0.7425 0.7046 0.150 Uiso 0.7 1 calc R U P
H28B H 1.0422 0.7977 0.6450 0.150 Uiso 0.7 1 calc R U P
H28C H 1.0936 0.8524 0.7143 0.150 Uiso 0.7 1 calc R U P
C29 C 0.7001(15) 0.4177(18) 0.2303(12) 0.083(7) Uiso 0.5 1 d D . P
H29 H 0.6750 0.4640 0.1963 0.099 Uiso 0.5 1 calc R U P
C30 C 0.7031(14) 0.3227(15) 0.3415(10) 0.071(6) Uiso 0.5 1 d D . P
H30A H 0.6680 0.3169 0.3755 0.106 Uiso 0.5 1 calc R U P
H30B H 0.7063 0.2615 0.3189 0.106 Uiso 0.5 1 calc R U P
H30C H 0.7598 0.3432 0.3664 0.106 Uiso 0.5 1 calc R U P
C31 C 0.5934(11) 0.4439(13) 0.2958(10) 0.054(5) Uiso 0.5 1 d D . P
H31A H 0.5762 0.4190 0.3371 0.081 Uiso 0.5 1 calc R U P
H31B H 0.6077 0.5109 0.3033 0.081 Uiso 0.5 1 calc R U P
H31C H 0.5471 0.4367 0.2533 0.081 Uiso 0.5 1 calc R U P
C32 C 0.1800(15) 0.4687(19) 0.6089(12) 0.067(7) Uiso 0.4 1 d D . P
H32 H 0.1411 0.5170 0.5891 0.081 Uiso 0.4 1 calc R U P
C33 C 0.0948(15) 0.4375(19) 0.6975(16) 0.077(8) Uiso 0.4 1 d D . P
H33A H 0.1001 0.3963 0.7388 0.115 Uiso 0.4 1 calc R U P
H33B H 0.0932 0.5035 0.7122 0.115 Uiso 0.4 1 calc R U P
H33C H 0.0427 0.4224 0.6619 0.115 Uiso 0.4 1 calc R U P
C34 C 0.2121(18) 0.3323(17) 0.6881(16) 0.081(8) Uiso 0.4 1 d D . P
H34A H 0.1968 0.3078 0.7304 0.122 Uiso 0.4 1 calc R U P
H34B H 0.1958 0.2865 0.6492 0.122 Uiso 0.4 1 calc R U P
H34C H 0.2731 0.3427 0.6987 0.122 Uiso 0.4 1 calc R U P
C35 C 1.122(4) 0.404(4) 0.955(3) 0.091(19) Uiso 0.2 1 d D . P
C36 C 1.035(3) 0.415(4) 1.048(2) 0.060(13) Uiso 0.2 1 d D . P
C37 C 0.997(4) 0.524(5) 0.971(4) 0.11(2) Uiso 0.2 1 d D . P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Zn1 O4 143.8(3) . .
O1 Zn1 N2 95.9(3) . .
O4 Zn1 N2 108.9(3) . .
O1 Zn1 N1 99.9(3) . .
O4 Zn1 N1 99.0(3) . .
N2 Zn1 N1 104.3(3) . .
O1 Zn1 C14 122.3(3) . .
O4 Zn1 C14 28.7(4) . .
N2 Zn1 C14 100.9(3) . .
N1 Zn1 C14 127.5(3) . .
C1 O1 Zn1 117.8(6) . .
C14 O4 Zn1 104.2(7) . .
C15 N1 C19 116.9(7) . .
C15 N1 Zn1 125.1(5) . .
C19 N1 Zn1 117.9(6) . .
C21 N2 C25 116.2(7) . .
C21 N2 Zn1 118.7(5) . .
C25 N2 Zn1 124.7(6) . .
C17 N3 C20 124.7(7) . .
C23 N4 C20 127.1(7) . 4_565
C26 N5 C27 119.0(11) . .
C26 N5 C28 118.4(13) . .
C27 N5 C28 122.5(13) . .
C29 N6 C31 118.6(16) . .
C29 N6 C30 123.8(17) . .
C31 N6 C30 117.4(15) . .
C32 N7 C33 125.0(18) . .
C32 N7 C34 118.9(18) . .
C33 N7 C34 113.3(15) . .
C35 N8 C36 127(4) . .
C35 N8 C37 140(5) . .
C36 N8 C37 91(4) . .
C35 N8 C37 167(5) . 3_767
C36 N8 C37 40(3) . 3_767
C37 N8 C37 51(5) . 3_767
O2 C1 O1 126.0(7) . .
O2 C1 C2 120.3(8) . .
O1 C1 C2 113.7(8) . .
C7 C2 C3 119.4(8) . .
C7 C2 C1 120.4(8) . .
C3 C2 C1 120.2(9) . .
C2 C3 C4 119.9(10) . .
C5 C4 C3 121.3(9) . .
C6 C5 C4 117.3(8) . .
C6 C5 C8 120.5(9) . .
C4 C5 C8 122.0(8) . .
C5 C6 C7 122.1(10) . .
C2 C7 C6 119.7(9) . .
C10 C8 C9 118.8(9) . .
C10 C8 C5 120.9(9) . .
C9 C8 C5 120.2(9) . .
C8 C9 C11 117.2(12) . .
C8 C10 C13 122.1(10) . .
C12 C11 C9 124.0(12) . .
C11 C12 C13 118.0(9) . .
C11 C12 C14 122.2(10) . 4_576
C13 C12 C14 119.5(10) . 4_576
C12 C13 C10 119.7(11) . .
O3 C14 O4 122.3(9) . .
O3 C14 C12 121.1(10) . 4_675
O4 C14 C12 116.7(10) . 4_675
O3 C14 Zn1 75.2(5) . .
O4 C14 Zn1 47.1(5) . .
C12 C14 Zn1 163.8(9) 4_675 .
N1 C15 C16 124.8(8) . .
C17 C16 C15 118.0(8) . .
N3 C17 C16 126.4(8) . .
N3 C17 C18 115.8(7) . .
C16 C17 C18 117.8(7) . .
C19 C18 C17 118.7(8) . .
N1 C19 C18 123.7(9) . .
O5 C20 N3 126.0(8) . .
O5 C20 N4 123.7(8) . 4_666
N3 C20 N4 110.2(7) . 4_666
N2 C21 C22 124.0(7) . .
C21 C22 C23 119.5(7) . .
N4 C23 C22 117.8(7) . .
N4 C23 C24 126.0(7) . .
C22 C23 C24 116.2(7) . .
C25 C24 C23 120.5(7) . .
N2 C25 C24 123.5(7) . .
O6 C26 N5 125.2(13) . .
O7 C29 N6 116(2) . .
O8 C32 N7 126(2) . .
O9 C35 N8 121(5) . .
C37 C36 N8 71(5) 3_767 .
C36 C37 C37 132(9) 3_767 3_767
C36 C37 N8 161(8) 3_767 .
C37 C37 N8 65(4) 3_767 .
C36 C37 N8 68(4) 3_767 3_767
C37 C37 N8 64(5) 3_767 3_767
N8 C37 N8 129(5) . 3_767
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 1.915(5) .
Zn1 O4 1.951(7) .
Zn1 N2 2.039(7) .
Zn1 N1 2.072(7) .
Zn1 C14 2.582(9) .
O1 C1 1.304(10) .
O2 C1 1.213(11) .
O3 C14 1.254(14) .
O4 C14 1.280(13) .
O5 C20 1.191(10) .
O6 C26 1.187(13) .
O7 C29 1.235(18) .
O8 C32 1.186(17) .
O9 C35 1.24(2) .
N1 C15 1.307(11) .
N1 C19 1.331(10) .
N2 C21 1.342(11) .
N2 C25 1.349(9) .
N3 C17 1.378(10) .
N3 C20 1.389(11) .
N4 C23 1.353(10) .
N4 C20 1.409(10) 4_565
N5 C26 1.351(13) .
N5 C27 1.451(14) .
N5 C28 1.482(16) .
N6 C29 1.393(17) .
N6 C31 1.431(16) .
N6 C30 1.478(16) .
N7 C32 1.351(17) .
N7 C33 1.475(17) .
N7 C34 1.487(17) .
N8 C35 1.40(2) .
N8 C36 1.49(2) .
N8 C37 1.50(2) .
N8 C37 1.51(8) 3_767
C1 C2 1.515(11) .
C2 C7 1.360(14) .
C2 C3 1.368(12) .
C3 C4 1.393(12) .
C4 C5 1.371(14) .
C5 C6 1.362(13) .
C5 C8 1.481(11) .
C6 C7 1.389(13) .
C8 C10 1.338(15) .
C8 C9 1.377(15) .
C9 C11 1.418(15) .
C10 C13 1.404(13) .
C11 C12 1.317(18) .
C12 C13 1.356(15) .
C12 C14 1.506(12) 4_576
C14 C12 1.506(12) 4_675
C15 C16 1.390(11) .
C16 C17 1.379(12) .
C17 C18 1.401(13) .
C18 C19 1.372(12) .
C20 N4 1.409(10) 4_666
C21 C22 1.375(12) .
C22 C23 1.395(10) .
C23 C24 1.401(11) .
C24 C25 1.359(12) .
C36 C37 1.03(7) 3_767
C37 C36 1.03(7) 3_767
C37 C37 1.31(14) 3_767
C37 N8 1.51(8) 3_767
