#------------------------------------------------------------------------------
#$Date: 2016-03-22 22:06:50 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179032 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/30/4123061.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_4123061
loop_
_publ_author_name
'Blackburn, Anthea K.'
'Sue, Andrew C.-H.'
'Shveyd, Alexander K.'
'Cao, Dennis'
'Tayi, Alok'
'Narayanan, Ashwin'
'Rolczynski, Brian S.'
'Szarko, Jodi M.'
'Bozdemir, Ozgur A.'
'Wakabayashi, Rie'
'Lehrman, Jessica A.'
'Kahr, Bart'
'Chen, Lin X.'
'Nassar, Majed S.'
'Stupp, Samuel I.'
'Stoddart, J. Fraser'
_publ_section_title
;
 Lock-Arm Supramolecular Ordering: A Molecular Construction Set for
 Cocrystallizing Organic Charge Transfer Complexes.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              141124065827003
_journal_paper_doi               10.1021/ja509442t
_journal_year                    2014
_chemical_formula_moiety         'C18 H20 N2 O8, C16 H12 N2'
_chemical_formula_sum            'C34 H32 N4 O8'
_chemical_formula_weight         624.63
_chemical_name_systematic
;
 ?
;
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4866)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.8960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9937(2)
_cell_length_b                   11.8675(2)
_cell_length_c                   17.5154(3)
_cell_measurement_reflns_used    8580
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.61
_cell_measurement_theta_min      3.72
_cell_volume                     1427.53(5)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.99
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Quazar optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15493
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.218
_diffrn_reflns_theta_min         4.526
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.869
_exptl_absorpt_correction_T_max  0.4665
_exptl_absorpt_correction_T_min  0.3565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0689 before and 0.0373 after correction.
The Ratio of minimum to maximum transmission is 0.7642.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0541
_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/[σ²(Fo²)+(0.0760P)²+1.7440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1497
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2290
_reflns_number_total             2479
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja509442t_si_004.cif
_cod_data_source_block           p21-n
_cod_database_code               4123061
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-4
_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_max   0.938
_shelx_estimated_absorpt_t_min   0.654
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C14(H14), C15(H15), C17(H17)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'
#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
O1 O -0.2938(3) 0.50453(16) 0.56341(11) 0.0406(5) Uani 1 1 d .
O2 O 0.2016(2) 0.49690(12) 0.66613(8) 0.0256(4) Uani 1 1 d .
O3 O 0.4276(2) 0.66842(13) 0.81334(9) 0.0303(4) Uani 1 1 d .
O4 O 0.5960(2) 0.29667(13) 0.84491(9) 0.0320(4) Uani 1 1 d .
N1 N 0.5105(3) 0.47964(15) 0.80932(10) 0.0249(4) Uani 1 1 d .
C1 C -0.1177(3) 0.5469(2) 0.60715(13) 0.0296(5) Uani 1 1 d .
H1A H -0.1391 0.5746 0.6582 0.035 Uiso 1 1 calc R
H1B H -0.0701 0.6104 0.5792 0.035 Uiso 1 1 calc R
C2 C 0.0300(3) 0.45303(19) 0.61858(13) 0.0276(5) Uani 1 1 d .
H2A H -0.0195 0.3879 0.6443 0.033 Uiso 1 1 calc R
H2B H 0.0577 0.4280 0.5679 0.033 Uiso 1 1 calc R
C3 C 0.3578(3) 0.41757(19) 0.67638(13) 0.0277(5) Uani 1 1 d .
H3A H 0.3904 0.3981 0.6254 0.033 Uiso 1 1 calc R
H3B H 0.3191 0.3477 0.7003 0.033 Uiso 1 1 calc R
C4 C 0.5327(3) 0.4698(2) 0.72853(13) 0.0275(5) Uani 1 1 d .
H4A H 0.6491 0.4234 0.7262 0.033 Uiso 1 1 calc R
H4B H 0.5553 0.5457 0.7085 0.033 Uiso 1 1 calc R
C5 C 0.4662(3) 0.57871(18) 0.84499(13) 0.0251(5) Uani 1 1 d .
C6 C 0.5514(3) 0.39042(18) 0.86185(13) 0.0257(5) Uani 1 1 d .
C7 C 0.4775(3) 0.54956(18) 0.92883(12) 0.0232(5) Uani 1 1 d .
C8 C 0.5282(3) 0.43589(18) 0.93881(12) 0.0239(5) Uani 1 1 d .
C9 C 0.4476(3) 0.61744(18) 0.98954(12) 0.0245(5) Uani 1 1 d .
H9 H 0.4132 0.6947 0.9827 0.029 Uiso 1 1 calc R
N2 N 0.1194(3) 0.16030(17) 0.93448(14) 0.0334(5) Uani 1 1 d .
C10 C 0.0779(3) 0.3225(2) 0.84848(14) 0.0335(6) Uani 1 1 d .
H10 H 0.0992 0.2754 0.8070 0.040 Uiso 1 1 calc R
C11 C 0.0888(3) 0.2774(2) 0.92215(13) 0.0302(5) Uani 1 1 d .
C12 C 0.0574(3) 0.34732(19) 0.98332(13) 0.0272(5) Uani 1 1 d .
C13 C 0.0154(3) 0.4630(2) 0.97032(14) 0.0292(5) Uani 1 1 d .
C14 C 0.0714(3) 0.3063(2) 1.06234(14) 0.0340(6) Uani 1 1 d .
H14 H 0.1017 0.2293 1.0736 0.041 Uiso 1 1 calc R
C15 C 0.0417(3) 0.3762(2) 1.12047(13) 0.0335(6) Uani 1 1 d .
H15 H 0.0512 0.3463 1.1714 0.040 Uiso 1 1 calc R
C16 C -0.0030(3) 0.4925(2) 1.10795(14) 0.0321(5) Uani 1 1 d .
C17 C -0.0360(4) 0.5635(2) 1.16537(14) 0.0341(6) Uani 1 1 d .
H17 H -0.0303 0.5344 1.2163 0.041 Uiso 1 1 calc R
H2C H 0.184(5) 0.128(3) 0.894(2) 0.060(10) Uiso 1 1 d .
H2D H 0.175(4) 0.141(2) 0.9828(19) 0.041(8) Uiso 1 1 d .
H1 H -0.390(6) 0.561(4) 0.562(2) 0.079(12) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 O2 C3 111.89(16) . .
C5 N1 C4 125.21(18) . .
C5 N1 C6 112.30(18) . .
C6 N1 C4 122.20(19) . .
O1 C1 C2 108.33(19) . .
O2 C2 C1 106.76(18) . .
O2 C3 C4 108.52(18) . .
N1 C4 C3 113.35(18) . .
O3 C5 N1 126.0(2) . .
O3 C5 C7 128.3(2) . .
N1 C5 C7 105.67(18) . .
O4 C6 N1 124.5(2) . .
O4 C6 C8 129.3(2) . .
N1 C6 C8 106.14(18) . .
C8 C7 C5 108.11(19) . .
C9 C7 C5 129.3(2) . .
C9 C7 C8 122.6(2) . .
C7 C8 C6 107.77(18) . .
C9 C8 C6 129.7(2) 3_667 .
C9 C8 C7 122.6(2) 3_667 .
C7 C9 C8 114.8(2) . 3_667
C11 C10 C17 120.6(2) . 3_567
C10 C11 N2 120.0(2) . .
C10 C11 C12 119.6(2) . .
C12 C11 N2 120.2(2) . .
C11 C12 C13 120.5(2) . .
C11 C12 C14 122.5(2) . .
C13 C12 C14 117.0(2) . .
C12 C13 C16 118.5(2) . 3_567
C13 C13 C12 122.9(3) 3_567 .
C13 C13 C16 118.6(3) 3_567 3_567
C15 C14 C12 121.1(2) . .
C14 C15 C16 122.5(2) . .
C15 C16 C13 118.0(2) . 3_567
C17 C16 C13 118.8(2) . 3_567
C17 C16 C15 123.2(2) . .
C16 C17 C10 122.0(2) . 3_567
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.414(3) .
O2 C2 1.424(3) .
O2 C3 1.428(3) .
O3 C5 1.207(3) .
O4 C6 1.208(3) .
N1 C4 1.457(3) .
N1 C5 1.394(3) .
N1 C6 1.396(3) .
C1 C2 1.506(3) .
C3 C4 1.514(3) .
C5 C7 1.496(3) .
C6 C8 1.489(3) .
C7 C8 1.397(3) .
C7 C9 1.381(3) .
C8 C9 1.387(3) 3_667
C9 C8 1.387(3) 3_667
N2 C11 1.417(3) .
C10 C11 1.385(3) .
C10 C17 1.396(4) 3_567
C11 C12 1.404(3) .
C12 C13 1.413(3) .
C12 C14 1.453(3) .
C13 C13 1.409(5) 3_567
C13 C16 1.456(3) 3_567
C14 C15 1.359(4) .
C15 C16 1.423(4) .
C16 C13 1.456(3) 3_567
C16 C17 1.364(4) .
C17 C10 1.396(4) 3_567
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C1 C2 O2 -177.01(17) . .
O2 C3 C4 N1 71.5(2) . .
O3 C5 C7 C8 -179.6(2) . .
O3 C5 C7 C9 -0.3(4) . .
O4 C6 C8 C7 179.3(2) . .
O4 C6 C8 C9 0.3(4) . 3_667
N1 C5 C7 C8 0.2(2) . .
N1 C5 C7 C9 179.6(2) . .
N1 C6 C8 C7 -0.8(2) . .
N1 C6 C8 C9 -179.8(2) . 3_667
C2 O2 C3 C4 -179.00(17) . .
C3 O2 C2 C1 -175.72(17) . .
C4 N1 C5 O3 5.1(3) . .
C4 N1 C5 C7 -174.75(18) . .
C4 N1 C6 O4 -4.9(3) . .
C4 N1 C6 C8 175.15(18) . .
C5 N1 C4 C3 -102.7(2) . .
C5 N1 C6 O4 -179.1(2) . .
C5 N1 C6 C8 1.0(2) . .
C5 C7 C8 C6 0.3(2) . .
C5 C7 C8 C9 179.42(19) . 3_667
C5 C7 C9 C8 -179.3(2) . 3_667
C6 N1 C4 C3 83.9(2) . .
C6 N1 C5 O3 179.1(2) . .
C6 N1 C5 C7 -0.8(2) . .
C8 C7 C9 C8 0.0(3) . 3_667
C9 C7 C8 C6 -179.07(19) . .
C9 C7 C8 C9 0.0(4) . 3_667
N2 C11 C12 C13 -176.2(2) . .
N2 C11 C12 C14 5.5(3) . .
C10 C11 C12 C13 -0.1(3) . .
C10 C11 C12 C14 -178.4(2) . .
C11 C12 C13 C13 -179.4(3) . 3_567
C11 C12 C13 C16 0.8(3) . 3_567
C11 C12 C14 C15 179.5(2) . .
C12 C14 C15 C16 -0.4(4) . .
C13 C12 C14 C15 1.1(3) . .
C13 C16 C17 C10 -1.1(4) 3_567 3_567
C14 C12 C13 C13 -1.0(4) . 3_567
C14 C12 C13 C16 179.2(2) . 3_567
C14 C15 C16 C13 -0.5(3) . 3_567
C14 C15 C16 C17 179.0(2) . .
C15 C16 C17 C10 179.4(2) . 3_567
C17 C10 C11 N2 176.1(2) 3_567 .
C17 C10 C11 C12 0.0(3) 3_567 .
