#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558201.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_1558201
loop_
_publ_author_name
'Ding, Xiaodan'
'Unruh, Daniel K.'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Controlling thermal expansion within mixed cocrystals by tuning molecular
 motion capability
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02795B
_journal_year                    2020
_chemical_formula_sum            'C18 H14.58 N2 O2'
_chemical_formula_weight         290.9
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-02T10:38:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.3825(12)
_cell_angle_beta                 108.0580(14)
_cell_angle_gamma                114.4899(17)
_cell_formula_units_Z            2
_cell_length_a                   8.20354(16)
_cell_length_b                   9.82973(15)
_cell_length_c                   10.95062(15)
_cell_measurement_reflns_used    10087
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      77.123
_cell_measurement_theta_min      4.314
_cell_volume                     749.11(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1810864
_diffrn_orient_matrix_UB_12      -0.0489953
_diffrn_orient_matrix_UB_13      0.0356887
_diffrn_orient_matrix_UB_21      0.1268521
_diffrn_orient_matrix_UB_22      0.0761251
_diffrn_orient_matrix_UB_23      0.1441907
_diffrn_orient_matrix_UB_31      -0.0069403
_diffrn_orient_matrix_UB_32      0.1504868
_diffrn_orient_matrix_UB_33      -0.0266988
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14771
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.402
_diffrn_reflns_theta_min         4.331
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.90605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.29
_exptl_crystal_description       irregular
_exptl_crystal_F_000             305
_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0038(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     438
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0510P)²+0.0519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0
_reflns_number_gt                2750
_reflns_number_total             3099
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE25_BA75_250
_cod_original_cell_volume        749.11(2)
_cod_database_code               1558201
_shelx_estimated_absorpt_t_min   0.869
_shelx_estimated_absorpt_t_max   0.946
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16828(10) 0.14646(9) 0.30450(7) 0.0538(2) Uani 1 1 d . . . . .
H1 H 0.201072 0.171628 0.38492 0.081 Uiso 1 1 calc R U . . .
O2 O 0.81743(11) 0.21572(10) 0.43280(8) 0.0620(2) Uani 1 1 d . . . . .
H2A H 0.822066 0.250374 0.504883 0.093 Uiso 1 1 calc R U . . .
N1 N 0.26257(13) 0.24192(11) -0.43241(8) 0.0545(2) Uani 1 1 d . . . . .
C1 C 0.31818(14) 0.14648(10) 0.27607(9) 0.0440(2) Uani 1 1 d . . . . .
C2 C 0.49240(14) 0.17984(10) 0.37331(9) 0.0443(2) Uani 1 1 d . . . . .
H2 H 0.508463 0.202411 0.461764 0.053 Uiso 1 1 calc R U . . .
C3 C 0.64354(15) 0.18011(11) 0.34080(10) 0.0475(2) Uani 1 1 d . . . . .
C4 C 0.61868(17) 0.14337(12) 0.21009(11) 0.0560(3) Uani 1 1 d . . . . .
H4 H 0.719017 0.141081 0.187205 0.067 Uiso 1 1 calc R U . . .
C5 C 0.44447(19) 0.11039(13) 0.11465(10) 0.0599(3) Uani 1 1 d . . . . .
H5 H 0.427655 0.086324 0.026229 0.072 Uiso 1 1 calc R U . . .
C6 C 0.29373(17) 0.11172(12) 0.14543(10) 0.0545(3) Uani 1 1 d . . . . .
H6 H 0.176351 0.089399 0.078802 0.065 Uiso 1 1 calc R U . . .
C7 C 0.19747(16) 0.14725(12) -0.35629(10) 0.0533(3) Uani 1 1 d . . . . .
H7 H 0.153672 0.042415 -0.384319 0.064 Uiso 1 1 calc R U . . .
C8 C 0.19105(15) 0.19508(12) -0.23870(10) 0.0503(2) Uani 1 1 d . . . . .
H8 H 0.142851 0.12399 -0.188554 0.06 Uiso 1 1 calc R U . . .
C9 C 0.25658(13) 0.34949(11) -0.19507(9) 0.0457(2) Uani 1 1 d D . . . .
C10 C 0.32965(16) 0.44931(12) -0.27208(11) 0.0530(3) Uani 1 1 d . . . . .
H10 H 0.379265 0.555083 -0.244923 0.064 Uiso 1 1 calc R U . . .
C11 C 0.32808(16) 0.39059(13) -0.38866(11) 0.0567(3) Uani 1 1 d . . . . .
H11 H 0.375906 0.459018 -0.440756 0.068 Uiso 1 1 calc R U . . .
C12 C 0.221(2) 0.3822(11) -0.0680(13) 0.0405(16) Uani 0.291(11) 1 d D U P A 1
H12 H 0.16367 0.298755 -0.030891 0.049 Uiso 0.291(11) 1 calc R U P A 1
C13 C 0.2634(8) 0.5150(9) -0.0108(7) 0.0405(12) Uani 0.291(11) 1 d D U P A 1
H13 H 0.32562 0.595984 -0.048287 0.049 Uiso 0.291(11) 1 calc R U P A 1
C14A C 0.228(2) 0.5607(13) 0.1100(10) 0.0407(19) Uani 0.291(11) 1 d DG U P A 1
C15A C 0.148(2) 0.4500(11) 0.1774(12) 0.047(2) Uani 0.291(11) 1 d G U P A 1
H15A H 0.116063 0.34772 0.14857 0.056 Uiso 0.291(11) 1 calc R U P A 1
C16A C 0.115(2) 0.4906(13) 0.2875(11) 0.046(2) Uani 0.291(11) 1 d G U P A 1
H16A H 0.061485 0.415822 0.333101 0.056 Uiso 0.291(11) 1 calc R U P A 1
N2A N 0.163(2) 0.6419(15) 0.3302(11) 0.043(2) Uani 0.291(11) 1 d G U P A 1
C17A C 0.242(2) 0.7526(11) 0.2628(12) 0.046(2) Uani 0.291(11) 1 d G U P A 1
H17A H 0.274304 0.854864 0.291648 0.055 Uiso 0.291(11) 1 calc R U P A 1
C18A C 0.275(2) 0.7119(12) 0.1527(12) 0.046(2) Uani 0.291(11) 1 d G U P A 1
H18A H 0.328884 0.786766 0.107116 0.056 Uiso 0.291(11) 1 calc R U P A 1
C14B C 0.2151(8) 0.5275(6) 0.1223(4) 0.0441(9) Uani 0.709(11) 1 d D U P A 2
C15B C 0.1271(9) 0.4419(5) 0.2020(5) 0.0487(8) Uani 0.709(11) 1 d . U P A 2
H15B H 0.078714 0.335269 0.186013 0.058 Uiso 0.709(11) 1 calc R U P A 2
C16B C 0.1119(9) 0.5155(6) 0.3045(5) 0.0485(9) Uani 0.709(11) 1 d . U P A 2
H16B H 0.050369 0.455217 0.356203 0.058 Uiso 0.709(11) 1 calc R U P A 2
N2B N 0.1774(9) 0.6645(6) 0.3355(5) 0.0510(10) Uani 0.709(11) 1 d . U P A 2
C17B C 0.2610(9) 0.7436(5) 0.2594(6) 0.0529(10) Uani 0.709(11) 1 d . U P A 2
H17B H 0.31041 0.850145 0.279539 0.064 Uiso 0.709(11) 1 calc R U P A 2
C18B C 0.2820(8) 0.6838(6) 0.1535(5) 0.0477(8) Uani 0.709(11) 1 d . U P A 2
H18B H 0.340965 0.747762 0.102588 0.057 Uiso 0.709(11) 1 calc R U P A 2
C19 C 0.2517(9) 0.4132(7) -0.0798(6) 0.0513(10) Uani 0.709(11) 1 d D U P A 2
C20 C 0.2335(4) 0.4610(5) 0.0143(3) 0.0511(7) Uani 0.709(11) 1 d D U P A 2
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 6 -1 0.0431
5 -4 -4 0.0754
5 0 0 0.0393
1 -5 5 0.0478
0 -3 -5 0.0753
0 3 -6 0.0824
-5 0 0 0.0431
2 -6 2 0.0449
2 4 -1 0.0344
-3 -3 5 0.0681
5 -4 1 0.0424
3 -4 4 0.0384
3 0 4 0.0674
-3 -1 -4 0.0729
-1 1 7 0.0918
-1 -2 7 0.0812
3 -4 -5 0.0856
0 5 -4 0.0552
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
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C7 N1 C11 117.01(9) . . ?
O1 C1 C2 121.88(8) . . ?
O1 C1 C6 118.29(9) . . ?
C2 C1 C6 119.83(10) . . ?
C1 C2 C3 120.43(9) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.20(9) . . ?
O2 C3 C4 117.93(9) . . ?
C2 C3 C4 119.87(10) . . ?
C5 C4 C3 118.93(10) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.83(10) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.10(10) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
N1 C7 C8 123.36(10) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C7 C8 C9 119.20(10) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C8 C9 C10 117.79(9) . . ?
C8 C9 C19 125.1(3) . . ?
C10 C9 C19 117.1(3) . . ?
C8 C9 C12 112.5(4) . . ?
C10 C9 C12 129.6(4) . . ?
C11 C10 C9 118.75(10) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.85(10) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 124.3(10) . . ?
C13 C12 H12 117.8 . . ?
C9 C12 H12 117.8 . . ?
C12 C13 C14A 129.2(10) . . ?
C12 C13 H13 115.4 . . ?
C14A C13 H13 115.4 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 119.6(6) . . ?
C18A C14A C13 120.4(6) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
N2A C16A C15A 120 . . ?
N2A C16A H16A 120 . . ?
C15A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C18B C14B C15B 116.4(2) . . ?
C18B C14B C20 120.9(3) . . ?
C15B C14B C20 122.7(3) . . ?
C16B C15B C14B 119.1(2) . . ?
C16B C15B H15B 120.4 . . ?
C14B C15B H15B 120.4 . . ?
N2B C16B C15B 124.8(2) . . ?
N2B C16B H16B 117.6 . . ?
C15B C16B H16B 117.6 . . ?
C17B N2B C16B 115.2(2) . . ?
N2B C17B C18B 125.5(2) . . ?
N2B C17B H17B 117.2 . . ?
C18B C17B H17B 117.2 . . ?
C17B C18B C14B 119.0(2) . . ?
C17B C18B H18B 120.5 . . ?
C14B C18B H18B 120.5 . . ?
C20 C19 C9 175.3(6) . . ?
C19 C20 C14B 175.8(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3588(12) . ?
O1 H1 0.83 . ?
O2 C3 1.3558(13) . ?
O2 H2A 0.83 . ?
N1 C7 1.3322(15) . ?
N1 C11 1.3360(15) . ?
C1 C2 1.3867(14) . ?
C1 C6 1.3886(14) . ?
C2 C3 1.3910(14) . ?
C2 H2 0.94 . ?
C3 C4 1.3914(14) . ?
C4 C5 1.3789(17) . ?
C4 H4 0.94 . ?
C5 C6 1.3836(17) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3762(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3874(14) . ?
C8 H8 0.94 . ?
C9 C10 1.3885(15) . ?
C9 C19 1.405(5) . ?
C9 C12 1.556(12) . ?
C10 C11 1.3731(16) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.279(12) . ?
C12 H12 0.94 . ?
C13 C14A 1.528(9) . ?
C13 H13 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C18B 1.385(4) . ?
C14B C15B 1.392(4) . ?
C14B C20 1.407(4) . ?
C15B C16B 1.375(4) . ?
C15B H15B 0.94 . ?
C16B N2B 1.320(3) . ?
C16B H16B 0.94 . ?
N2B C17B 1.318(3) . ?
C17B C18B 1.368(3) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.190(6) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.92 2.7515(11) 174.1 1_556 yes
O2 H2A N2A^a 0.83 2 2.82(6) 172.7 2_666 yes
O2 H2A N2B^b 0.83 1.9 2.733(4) 176.3 2_666 yes
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.46(8) . . . . ?
C6 C1 C2 C3 0.60(14) . . . . ?
C1 C2 C3 O2 178.37(9) . . . . ?
C1 C2 C3 C4 -1.44(15) . . . . ?
O2 C3 C4 C5 -178.44(10) . . . . ?
C2 C3 C4 C5 1.38(16) . . . . ?
C3 C4 C5 C6 -0.50(17) . . . . ?
C4 C5 C6 C1 -0.33(17) . . . . ?
O1 C1 C6 C5 -179.66(9) . . . . ?
C2 C1 C6 C5 0.28(15) . . . . ?
C11 N1 C7 C8 1.53(16) . . . . ?
N1 C7 C8 C9 -0.55(16) . . . . ?
C7 C8 C9 C10 -1.25(15) . . . . ?
C7 C8 C9 C19 177.5(4) . . . . ?
C7 C8 C9 C12 174.4(7) . . . . ?
C8 C9 C10 C11 1.99(15) . . . . ?
C19 C9 C10 C11 -176.9(3) . . . . ?
C12 C9 C10 C11 -172.7(8) . . . . ?
C7 N1 C11 C10 -0.72(16) . . . . ?
C9 C10 C11 N1 -1.04(17) . . . . ?
C8 C9 C12 C13 -178.1(11) . . . . ?
C10 C9 C12 C13 -3.1(18) . . . . ?
C9 C12 C13 C14A 177.1(10) . . . . ?
C12 C13 C14A C15A 4.2(15) . . . . ?
C12 C13 C14A C18A -175.9(12) . . . . ?
C18A C14A C15A C16A 0 . . . . ?
C13 C14A C15A C16A 179.9(11) . . . . ?
C14A C15A C16A N2A 0 . . . . ?
C15A C16A N2A C17A 0 . . . . ?
C16A N2A C17A C18A 0 . . . . ?
N2A C17A C18A C14A 0 . . . . ?
C15A C14A C18A C17A 0 . . . . ?
C13 C14A C18A C17A -179.9(11) . . . . ?
C18B C14B C15B C16B 0.0(3) . . . . ?
C20 C14B C15B C16B -178.9(5) . . . . ?
C14B C15B C16B N2B -0.8(3) . . . . ?
C15B C16B N2B C17B 0.5(3) . . . . ?
C16B N2B C17B C18B 0.7(3) . . . . ?
N2B C17B C18B C14B -1.5(4) . . . . ?
C15B C14B C18B C17B 1.0(3) . . . . ?
C20 C14B C18B C17B 180.0(5) . . . . ?
