#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558226.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_1558226
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            'C16.49 H14 N3.51 O2'
_chemical_formula_weight         293.28
_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             2019-11-07T15:24:17-00:00
_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                93.656(2)
_cell_angle_beta                 106.798(3)
_cell_angle_gamma                113.712(3)
_cell_formula_units_Z            2
_cell_length_a                   8.0696(2)
_cell_length_b                   9.7563(3)
_cell_length_c                   10.8866(3)
_cell_measurement_reflns_used    5535
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      76.316
_cell_measurement_theta_min      4.317
_cell_volume                     735.24(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (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      270(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.948
_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      -0.0435655
_diffrn_orient_matrix_UB_12      -0.114365
_diffrn_orient_matrix_UB_13      0.0908631
_diffrn_orient_matrix_UB_21      -0.1908603
_diffrn_orient_matrix_UB_22      -0.1078992
_diffrn_orient_matrix_UB_23      -0.1093169
_diffrn_orient_matrix_UB_31      0.1048894
_diffrn_orient_matrix_UB_32      -0.0795753
_diffrn_orient_matrix_UB_33      -0.051046
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12366
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.124
_diffrn_reflns_theta_min         4.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       plate
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0041(10)
_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   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     507
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0462
_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)+(0.0695P)²+0.0834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1378
_reflns_Friedel_coverage         0
_reflns_number_gt                2337
_reflns_number_total             2962
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           A75_BA25_270
_cod_original_cell_volume        735.23(4)
_cod_database_code               1558226
_shelx_estimated_absorpt_t_min   0.863
_shelx_estimated_absorpt_t_max   0.981
_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 0.16709(16) 0.15440(13) 0.31196(11) 0.0634(3) Uani 1 1 d . . . . .
H1 H 0.196978 0.175193 0.391833 0.095 Uiso 1 1 calc R U . . .
O2 O 0.81877(18) 0.21741(16) 0.43483(12) 0.0747(4) Uani 1 1 d . . . . .
H2A H 0.823263 0.254559 0.506123 0.112 Uiso 1 1 calc R U . . .
N1 N 0.2609(2) 0.24762(16) -0.42120(13) 0.0617(4) Uani 1 1 d . . . . .
C1 C 0.3179(2) 0.15135(15) 0.28177(14) 0.0512(4) Uani 1 1 d . . . . .
C2 C 0.4924(2) 0.18373(16) 0.37790(14) 0.0524(4) Uani 1 1 d . . . . .
H2 H 0.507722 0.206896 0.465868 0.063 Uiso 1 1 calc R U . . .
C3 C 0.6439(2) 0.18169(17) 0.34339(15) 0.0557(4) Uani 1 1 d . . . . .
C4 C 0.6201(3) 0.14295(19) 0.21285(16) 0.0635(4) Uani 1 1 d . . . . .
H4 H 0.719979 0.138554 0.189076 0.076 Uiso 1 1 calc R U . . .
C5 C 0.4455(3) 0.11095(19) 0.11854(16) 0.0667(5) Uani 1 1 d . . . . .
H5 H 0.429511 0.085965 0.030666 0.08 Uiso 1 1 calc R U . . .
C6 C 0.2938(3) 0.11492(18) 0.15075(15) 0.0609(4) Uani 1 1 d . . . . .
H6 H 0.177533 0.093515 0.085655 0.073 Uiso 1 1 calc R U . . .
C7 C 0.3266(3) 0.3967(2) -0.37319(19) 0.0679(4) Uani 1 1 d . . . . .
H7 H 0.376178 0.46629 -0.422751 0.082 Uiso 1 1 calc R U . . .
C8 C 0.3248(3) 0.45260(19) -0.25481(18) 0.0670(5) Uani 1 1 d . . . . .
H8 H 0.373292 0.557185 -0.224363 0.08 Uiso 1 1 calc R U . . .
C9 C 0.2488(2) 0.34878(19) -0.18240(15) 0.0572(4) Uani 1 1 d D . . . .
C10 C 0.1836(2) 0.19499(18) -0.22938(16) 0.0600(4) Uani 1 1 d . . . . .
H10 H 0.134125 0.123112 -0.181479 0.072 Uiso 1 1 calc R U . . .
C11 C 0.1930(2) 0.15024(19) -0.34764(16) 0.0609(4) Uani 1 1 d . . . . .
H11 H 0.149884 0.046424 -0.378415 0.073 Uiso 1 1 calc R U . . .
N2A N 0.2124(9) 0.3769(5) -0.0571(5) 0.0516(12) Uani 0.638(13) 1 d D U P A 1
N3A N 0.2659(5) 0.5137(5) -0.0166(5) 0.0530(11) Uani 0.638(13) 1 d D U P A 1
C12A C 0.2324(10) 0.5542(7) 0.1010(6) 0.0458(10) Uani 0.638(13) 1 d . U P A 1
C13A C 0.2856(13) 0.7060(7) 0.1467(6) 0.0566(11) Uani 0.638(13) 1 d . U P A 1
H13A H 0.34202 0.780975 0.103384 0.068 Uiso 0.638(13) 1 calc R U P A 1
C14A C 0.2524(14) 0.7430(6) 0.2584(8) 0.0612(17) Uani 0.638(13) 1 d . U P A 1
H14A H 0.289584 0.84581 0.28916 0.073 Uiso 0.638(13) 1 calc R U P A 1
N4A N 0.1731(13) 0.6455(9) 0.3248(7) 0.0569(13) Uani 0.638(13) 1 d . U P A 1
C15A C 0.1218(12) 0.5007(9) 0.2781(7) 0.0554(11) Uani 0.638(13) 1 d . U P A 1
H15A H 0.063239 0.428661 0.322923 0.066 Uiso 0.638(13) 1 calc R U P A 1
C16A C 0.1481(9) 0.4481(5) 0.1688(6) 0.0512(11) Uani 0.638(13) 1 d . U P A 1
H16A H 0.110432 0.344539 0.141359 0.061 Uiso 0.638(13) 1 calc R U P A 1
C12B C 0.2067(18) 0.5155(12) 0.1192(9) 0.049(2) Uani 0.362(13) 1 d DG U P A 2
C13B C 0.279(2) 0.6739(12) 0.1454(12) 0.063(2) Uani 0.362(13) 1 d G U P A 2
H13B H 0.336032 0.730456 0.090941 0.075 Uiso 0.362(13) 1 calc R U P A 2
C14B C 0.265(2) 0.7476(11) 0.2528(14) 0.067(4) Uani 0.362(13) 1 d G U P A 2
H14B H 0.312902 0.853582 0.270299 0.08 Uiso 0.362(13) 1 calc R U P A 2
N4B N 0.179(2) 0.6630(15) 0.3342(12) 0.066(3) Uani 0.362(13) 1 d G U P A 2
C15B C 0.1071(19) 0.5047(15) 0.3080(11) 0.058(2) Uani 0.362(13) 1 d G U P A 2
H15B H 0.049746 0.448091 0.362448 0.07 Uiso 0.362(13) 1 calc R U P A 2
C16B C 0.1210(17) 0.4309(10) 0.2006(11) 0.057(2) Uani 0.362(13) 1 d G U P A 2
H16B H 0.072875 0.324961 0.183089 0.069 Uiso 0.362(13) 1 calc R U P A 2
C17 C 0.233(3) 0.461(3) 0.0194(12) 0.057(3) Uani 0.244(17) 1 d D U P A 2
C18 C 0.254(3) 0.416(3) -0.0750(15) 0.057(4) Uani 0.244(17) 1 d D U P A 2
N2B N 0.285(3) 0.476(4) -0.068(3) 0.058(4) Uani 0.117(10) 1 d D U P A 3
N3B N 0.185(3) 0.398(3) -0.008(3) 0.055(4) Uani 0.117(10) 1 d D U P A 3
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
-5 4 3 0.1092
4 -4 -4 0.116
-2 4 5 0.0741
0 5 -5 0.001
3 3 -3 0.045
4 -1 1 0.0687
0 -5 5 0.0227
-4 1 -1 0.0879
0 -4 -4 0.1248
3 -5 -4 0.107
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 . . ?
C11 N1 C7 117.12(14) . . ?
O1 C1 C6 118.09(14) . . ?
O1 C1 C2 121.88(13) . . ?
C6 C1 C2 120.03(14) . . ?
C3 C2 C1 120.28(14) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
O2 C3 C4 118.03(15) . . ?
O2 C3 C2 121.86(14) . . ?
C4 C3 C2 120.11(15) . . ?
C5 C4 C3 118.79(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.00(15) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.77(15) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
N1 C7 C8 123.62(17) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 117.96(16) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C18 C9 C10 129.3(13) . . ?
C18 C9 C8 111.6(13) . . ?
C10 C9 C8 119.13(15) . . ?
C10 C9 N2A 111.8(2) . . ?
C8 C9 N2A 129.0(2) . . ?
C10 C9 N2B 147.0(7) . . ?
C8 C9 N2B 93.8(7) . . ?
C11 C10 C9 118.73(16) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.40(15) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 112.0(7) . . ?
N2A N3A C12A 116.9(7) . . ?
C13A C12A C16A 118.4(3) . . ?
C13A C12A N3A 118.4(4) . . ?
C16A C12A N3A 123.2(4) . . ?
C14A C13A C12A 117.8(4) . . ?
C14A C13A H13A 121.1 . . ?
C12A C13A H13A 121.1 . . ?
N4A C14A C13A 125.2(3) . . ?
N4A C14A H14A 117.4 . . ?
C13A C14A H14A 117.4 . . ?
C14A N4A C15A 115.7(3) . . ?
N4A C15A C16A 125.1(4) . . ?
N4A C15A H15A 117.4 . . ?
C16A C15A H15A 117.4 . . ?
C15A C16A C12A 117.7(3) . . ?
C15A C16A H16A 121.2 . . ?
C12A C16A H16A 121.2 . . ?
C17 C12B C13B 114.3(12) . . ?
C17 C12B C16B 125.7(12) . . ?
C13B C12B C16B 120 . . ?
C12B C13B C14B 120 . . ?
C12B C13B H13B 120 . . ?
C14B C13B H13B 120 . . ?
C13B C14B N4B 120 . . ?
C13B C14B H14B 120 . . ?
N4B C14B H14B 120 . . ?
C15B N4B C14B 120 . . ?
N4B C15B C16B 120 . . ?
N4B C15B H15B 120 . . ?
C16B C15B H15B 120 . . ?
C15B C16B C12B 120 . . ?
C15B C16B H16B 120 . . ?
C12B C16B H16B 120 . . ?
C18 C17 C12B 177(3) . . ?
C17 C18 C9 170(3) . . ?
N3B N2B C9 101(3) . . ?
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 1.3600(18) . ?
O1 H1 0.82 . ?
O2 C3 1.3610(19) . ?
O2 H2A 0.82 . ?
N1 C11 1.333(2) . ?
N1 C7 1.339(2) . ?
C1 C6 1.385(2) . ?
C1 C2 1.388(2) . ?
C2 C3 1.386(2) . ?
C2 H2 0.93 . ?
C3 C4 1.384(2) . ?
C4 C5 1.381(3) . ?
C4 H4 0.93 . ?
C5 C6 1.381(3) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.373(3) . ?
C7 H7 0.93 . ?
C8 C9 1.380(3) . ?
C8 H8 0.93 . ?
C9 C18 1.284(13) . ?
C9 C10 1.379(2) . ?
C9 N2A 1.507(6) . ?
C9 N2B 1.57(4) . ?
C10 C11 1.366(2) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
N2A N3A 1.229(6) . ?
N3A C12A 1.446(7) . ?
C12A C13A 1.377(5) . ?
C12A C16A 1.378(5) . ?
C13A C14A 1.376(5) . ?
C13A H13A 0.93 . ?
C14A N4A 1.304(5) . ?
C14A H14A 0.93 . ?
N4A C15A 1.320(5) . ?
C15A C16A 1.372(5) . ?
C15A H15A 0.93 . ?
C16A H16A 0.93 . ?
C12B C17 1.288(12) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C13B C14B 1.39 . ?
C13B H13B 0.93 . ?
C14B N4B 1.39 . ?
C14B H14B 0.93 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.93 . ?
C16B H16B 0.93 . ?
C17 C18 1.176(16) . ?
N2B N3B 1.239(19) . ?
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 0.82 1.96 2.7708(17) 172.5 1_556 yes
O2 H2A N4A 0.82 2.01 2.833(5) 176.2 2_666 yes
O2 H2A N4B 0.82 1.88 2.70(6) 177.3 2_666 yes
