#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558239.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_1558239
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            'C17.07 H15.07 N2.93 O2'
_chemical_formula_weight         293.25
_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             2020-03-05T13:01:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-07 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.4063(14)
_cell_angle_beta                 106.7767(15)
_cell_angle_gamma                114.0626(18)
_cell_formula_units_Z            2
_cell_length_a                   8.01388(15)
_cell_length_b                   9.81882(18)
_cell_length_c                   10.87660(17)
_cell_measurement_reflns_used    12908
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      76.96
_cell_measurement_theta_min      4.307
_cell_volume                     732.70(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.70a (Rigaku OD, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.957
_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      0.1320262
_diffrn_orient_matrix_UB_12      -0.0772047
_diffrn_orient_matrix_UB_13      0.0519688
_diffrn_orient_matrix_UB_21      0.0247934
_diffrn_orient_matrix_UB_22      0.0590436
_diffrn_orient_matrix_UB_23      0.1416779
_diffrn_orient_matrix_UB_31      -0.1794373
_diffrn_orient_matrix_UB_32      -0.1460916
_diffrn_orient_matrix_UB_33      -0.0069622
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            22578
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.356
_diffrn_reflns_theta_min         4.335
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.501
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.70a (Rigaku Oxford Diffraction, 2020)
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 light yellow'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       irregular
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0053(9)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2977
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0376
_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)+(0.0614P)²+0.0929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0
_reflns_number_gt                2557
_reflns_number_total             2977
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A50_BE50_210
_cod_original_cell_volume        732.70(2)
_cod_database_code               1558239
_shelx_estimated_absorpt_t_min   0.868
_shelx_estimated_absorpt_t_max   0.929
_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 0.16498(12) 0.15949(10) 0.30907(8) 0.0458(2) Uani 1 1 d . . . . .
H1 H 0.196935 0.184864 0.389693 0.069 Uiso 1 1 calc R U . . .
O2 O 0.82376(13) 0.22637(12) 0.43308(9) 0.0526(3) Uani 1 1 d . . . . .
H2A H 0.828035 0.263982 0.504971 0.079 Uiso 1 1 calc R U . . .
N1 N 0.26076(16) 0.24838(13) 0.57526(10) 0.0463(3) Uani 1 1 d . . . . .
N2A N 0.218(3) 0.3773(13) 0.9433(13) 0.0385(18) Uani 0.437(3) 1 d D U P A 1
N3A N 0.267(2) 0.5130(13) 0.9847(11) 0.0405(18) Uani 0.437(3) 1 d D U P A 1
C17 C 0.215(3) 0.3788(13) 0.9353(13) 0.0393(16) Uani 0.536(3) 1 d D U P A 2
H17 H 0.158942 0.300212 0.977192 0.047 Uiso 0.536(3) 1 calc DR U P A 2
C18 C 0.2658(19) 0.5200(13) 0.9881(11) 0.0373(14) Uani 0.536(3) 1 d D U P A 2
H18 H 0.325011 0.599265 0.947728 0.045 Uiso 0.536(3) 1 calc R U P A 2
N2B N 0.272(6) 0.466(6) 0.921(4) 0.040(3) Uani 0.0264(18) 1 d D U P A 3
N3B N 0.191(6) 0.412(5) 1.000(4) 0.041(3) Uani 0.0264(18) 1 d D U P A 3
N4 N 0.17560(15) 0.65081(12) 1.33044(10) 0.0441(3) Uani 1 1 d . . . . .
C1 C 0.31670(18) 0.15523(13) 0.27965(11) 0.0377(3) Uani 1 1 d . . . . .
C2 C 0.49383(17) 0.19145(13) 0.37594(11) 0.0377(3) Uani 1 1 d . . . . .
H2 H 0.510449 0.218369 0.464563 0.045 Uiso 1 1 calc R U . . .
C3 C 0.64728(18) 0.18814(14) 0.34206(11) 0.0404(3) Uani 1 1 d . . . . .
C4 C 0.6214(2) 0.14486(14) 0.21086(12) 0.0456(3) Uani 1 1 d . . . . .
H4 H 0.723104 0.140255 0.187117 0.055 Uiso 1 1 calc R U . . .
C5 C 0.4443(2) 0.10896(14) 0.11657(12) 0.0471(3) Uani 1 1 d . . . . .
H5 H 0.427052 0.080764 0.028023 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2909(2) 0.11319(14) 0.14843(11) 0.0445(3) Uani 1 1 d . . . . .
H6 H 0.171191 0.088078 0.082527 0.053 Uiso 1 1 calc R U . . .
C7 C 0.32273(19) 0.39558(15) 0.62494(13) 0.0470(3) Uani 1 1 d . . . . .
H7 H 0.371804 0.467775 0.575689 0.056 Uiso 1 1 calc R U . . .
C8 C 0.31864(19) 0.44723(15) 0.74429(12) 0.0445(3) Uani 1 1 d . . . . .
H8 H 0.365715 0.551902 0.775864 0.053 Uiso 1 1 calc R U . . .
C9 C 0.24335(17) 0.34105(14) 0.81684(11) 0.0381(3) Uani 1 1 d D . . . .
C10 C 0.18240(19) 0.18868(15) 0.76737(12) 0.0443(3) Uani 1 1 d . . . . .
H10 H 0.133563 0.114016 0.814753 0.053 Uiso 1 1 calc R U . . .
C11 C 0.19437(19) 0.14810(15) 0.64772(12) 0.0464(3) Uani 1 1 d . . . . .
H11 H 0.1537 0.04456 0.615606 0.056 Uiso 1 1 calc R U . . .
C12 C 0.23277(16) 0.55554(14) 1.10542(11) 0.0384(3) Uani 1 1 d D . . . .
C13 C 0.28691(19) 0.70727(15) 1.14967(12) 0.0457(3) Uani 1 1 d . . . . .
H13 H 0.343666 0.781072 1.103972 0.055 Uiso 1 1 calc R U . . .
C14 C 0.25687(19) 0.74942(15) 1.26161(13) 0.0477(3) Uani 1 1 d . . . . .
H14 H 0.295827 0.853292 1.290917 0.057 Uiso 1 1 calc R U . . .
C15 C 0.12178(18) 0.50349(15) 1.28708(12) 0.0433(3) Uani 1 1 d . . . . .
H15 H 0.063623 0.432205 1.334154 0.052 Uiso 1 1 calc R U . . .
C16 C 0.14762(18) 0.45103(15) 1.17625(12) 0.0430(3) Uani 1 1 d . . . . .
H16 H 0.108329 0.34663 1.149307 0.052 Uiso 1 1 calc DR U . . .
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
-4 -1 1 0.0681
3 3 -3 0.0873
0 6 -2 0.0863
4 1 -1 0.0905
-1 -2 -4 0.0457
0 -6 2 0.0494
2 2 -7 0.0731
-1 0 7 0.036
-2 1 -5 0.0681
0 4 -6 0.0553
3 0 4 0.092
4 -5 -3 0.1384
-3 6 2 0.1189
1 -3 -5 0.0535
0 0 -7 0.0505
-3 6 -2 0.1171
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 117.11(11) . . ?
N3A N2A C9 116.3(10) . . ?
N2A N3A C12 119.0(10) . . ?
C18 C17 C9 122.2(10) . . ?
C18 C17 H17 118.9 . . ?
C9 C17 H17 118.9 . . ?
C17 C18 C12 121.5(10) . . ?
C17 C18 H18 119.3 . . ?
C12 C18 H18 119.3 . . ?
N3B N2B C9 111(4) . . ?
N2B N3B C12 106(4) . . ?
C14 N4 C15 117.20(11) . . ?
O1 C1 C2 121.92(10) . . ?
O1 C1 C6 118.17(11) . . ?
C2 C1 C6 119.91(11) . . ?
C1 C2 C3 120.38(10) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.05(10) . . ?
O2 C3 C4 118.11(11) . . ?
C2 C3 C4 119.84(11) . . ?
C5 C4 C3 118.95(12) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.94(11) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.96(12) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.73(12) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.54(12) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 118.11(11) . . ?
C10 C9 C17 118.0(5) . . ?
C8 C9 C17 123.7(5) . . ?
C10 C9 N2A 116.8(5) . . ?
C8 C9 N2A 125.1(5) . . ?
C10 C9 N2B 151.0(15) . . ?
C8 C9 N2B 90.9(15) . . ?
C11 C10 C9 119.14(12) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.32(12) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 117.87(11) . . ?
C13 C12 C18 116.3(5) . . ?
C16 C12 C18 125.8(5) . . ?
C13 C12 N3A 118.3(5) . . ?
C16 C12 N3A 123.8(5) . . ?
C13 C12 N3B 154.4(13) . . ?
C16 C12 N3B 87.4(13) . . ?
C14 C13 C12 119.32(12) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 123.52(12) . . ?
N4 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N4 C15 C16 123.21(12) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.88(12) . . ?
C15 C16 H16 120.6 . . ?
C12 C16 H16 120.6 . . ?
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 1.3591(14) . ?
O1 H1 0.83 . ?
O2 C3 1.3549(15) . ?
O2 H2A 0.83 . ?
N1 C11 1.3345(18) . ?
N1 C7 1.3396(17) . ?
N2A N3A 1.236(7) . ?
N2A C9 1.492(11) . ?
N3A C12 1.488(10) . ?
C17 C18 1.315(7) . ?
C17 C9 1.423(11) . ?
C17 H17 0.94 . ?
C18 C12 1.427(11) . ?
C18 H18 0.94 . ?
N2B N3B 1.241(10) . ?
N2B C9 1.51(5) . ?
N3B C12 1.62(5) . ?
N4 C14 1.3325(18) . ?
N4 C15 1.3393(16) . ?
C1 C2 1.3872(16) . ?
C1 C6 1.3928(16) . ?
C2 C3 1.3935(17) . ?
C2 H2 0.94 . ?
C3 C4 1.3946(16) . ?
C4 C5 1.3781(19) . ?
C4 H4 0.94 . ?
C5 C6 1.3854(19) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3796(18) . ?
C7 H7 0.94 . ?
C8 C9 1.3904(18) . ?
C8 H8 0.94 . ?
C9 C10 1.3868(17) . ?
C10 C11 1.3796(17) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3807(18) . ?
C12 C16 1.3923(18) . ?
C13 C14 1.3792(18) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3852(17) . ?
C15 H15 0.94 . ?
C16 H16 0.94 . ?
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 1.93 2.7575(13) 176.8 . yes
O2 H2A N4 0.83 1.94 2.7729(13) 177.2 2_667 yes
