#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:19:29 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252960 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558238.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_1558238
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            'C17.09 H15.09 N2.91 O2'
_chemical_formula_weight         293.23
_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             2020-03-05T13:01:46-00:00
_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                93.5015(14)
_cell_angle_beta                 106.7347(15)
_cell_angle_gamma                114.0289(17)
_cell_formula_units_Z            2
_cell_length_a                   8.03047(14)
_cell_length_b                   9.82913(17)
_cell_length_c                   10.88163(17)
_cell_measurement_reflns_used    12143
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      77.245
_cell_measurement_theta_min      4.296
_cell_volume                     735.48(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      230(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.954
_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      0.1318913
_diffrn_orient_matrix_UB_12      -0.0769762
_diffrn_orient_matrix_UB_13      0.0518666
_diffrn_orient_matrix_UB_21      0.0247897
_diffrn_orient_matrix_UB_22      0.0591716
_diffrn_orient_matrix_UB_23      0.1416526
_diffrn_orient_matrix_UB_31      -0.1788721
_diffrn_orient_matrix_UB_32      -0.1459417
_diffrn_orient_matrix_UB_33      -0.0069018
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.954
_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            22021
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.346
_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    0.723
_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    1.324
_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         0.21
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0047(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   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2979
_refine_ls_number_restraints     306
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.039
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0548P)²+0.1088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0
_reflns_number_gt                2505
_reflns_number_total             2979
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b2.cif
_cod_data_source_block           A50_BE50_230
_cod_original_cell_volume        735.48(2)
_cod_database_code               1558238
_shelx_estimated_absorpt_t_min   0.869
_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 0.16537(13) 0.15867(11) 0.30913(9) 0.0504(3) Uani 1 1 d . . . . .
H1 H 0.196728 0.182987 0.389789 0.076 Uiso 1 1 calc R U . . .
O2 O 0.82284(14) 0.22612(13) 0.43286(9) 0.0579(3) Uani 1 1 d . . . . .
H2A H 0.828478 0.266325 0.504224 0.087 Uiso 1 1 calc R U . . .
N1 N 0.26047(17) 0.24819(14) 0.57517(11) 0.0504(3) Uani 1 1 d . . . . .
N2A N 0.220(3) 0.3761(15) 0.9431(13) 0.0416(17) Uani 0.416(3) 1 d D U P A 1
N3A N 0.268(2) 0.5106(15) 0.9854(14) 0.0425(18) Uani 0.416(3) 1 d D U P A 1
C17 C 0.214(2) 0.3798(14) 0.9357(12) 0.0421(15) Uani 0.544(3) 1 d D U P A 2
H17 H 0.155841 0.301901 0.977623 0.051 Uiso 0.544(3) 1 calc DR U P A 2
C18 C 0.265(2) 0.5214(14) 0.9868(13) 0.0405(13) Uani 0.544(3) 1 d D U P A 2
H18 H 0.322957 0.600334 0.94593 0.049 Uiso 0.544(3) 1 calc R U P A 2
N2B N 0.272(4) 0.465(4) 0.920(3) 0.043(3) Uani 0.0398(19) 1 d D U P A 3
N3B N 0.197(4) 0.412(4) 1.002(3) 0.045(3) Uani 0.0398(19) 1 d D U P A 3
N4 N 0.17604(16) 0.65058(13) 1.33058(10) 0.0477(3) Uani 1 1 d . . . . .
C1 C 0.31687(19) 0.15470(13) 0.27971(12) 0.0408(3) Uani 1 1 d . . . . .
C2 C 0.49359(18) 0.19103(14) 0.37567(11) 0.0414(3) Uani 1 1 d . . . . .
H2 H 0.510178 0.217985 0.464276 0.05 Uiso 1 1 calc R U . . .
C3 C 0.64663(19) 0.18794(14) 0.34195(12) 0.0437(3) Uani 1 1 d . . . . .
C4 C 0.6210(2) 0.14479(15) 0.21093(13) 0.0499(3) Uani 1 1 d . . . . .
H4 H 0.722594 0.140358 0.187129 0.06 Uiso 1 1 calc R U . . .
C5 C 0.4441(2) 0.10870(16) 0.11679(13) 0.0519(3) Uani 1 1 d . . . . .
H5 H 0.426817 0.080426 0.028259 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2913(2) 0.11285(15) 0.14868(12) 0.0485(3) Uani 1 1 d . . . . .
H6 H 0.171885 0.087764 0.082821 0.058 Uiso 1 1 calc R U . . .
C7 C 0.3224(2) 0.39510(17) 0.62484(14) 0.0517(3) Uani 1 1 d . . . . .
H7 H 0.371445 0.467019 0.575553 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3186(2) 0.44722(16) 0.74390(13) 0.0490(3) Uani 1 1 d . . . . .
H8 H 0.365432 0.551841 0.775267 0.059 Uiso 1 1 calc R U . . .
C9 C 0.24372(18) 0.34146(15) 0.81665(12) 0.0417(3) Uani 1 1 d D . . . .
C10 C 0.1828(2) 0.18946(16) 0.76724(13) 0.0484(3) Uani 1 1 d . . . . .
H10 H 0.133984 0.115041 0.814634 0.058 Uiso 1 1 calc R U . . .
C11 C 0.1944(2) 0.14855(16) 0.64779(13) 0.0505(3) Uani 1 1 d . . . . .
H11 H 0.153695 0.04503 0.615813 0.061 Uiso 1 1 calc R U . . .
C12 C 0.23250(18) 0.55497(15) 1.10561(12) 0.0423(3) Uani 1 1 d D . . . .
C13 C 0.2865(2) 0.70647(16) 1.14985(13) 0.0502(3) Uani 1 1 d . . . . .
H13 H 0.343056 0.780085 1.104137 0.06 Uiso 1 1 calc R U . . .
C14 C 0.2568(2) 0.74865(16) 1.26136(14) 0.0521(3) Uani 1 1 d . . . . .
H14 H 0.295581 0.852464 1.290504 0.063 Uiso 1 1 calc R U . . .
C15 C 0.12226(19) 0.50368(16) 1.28731(13) 0.0472(3) Uani 1 1 d . . . . .
H15 H 0.064228 0.432609 1.334387 0.057 Uiso 1 1 calc R U . . .
C16 C 0.1479(2) 0.45103(16) 1.17645(13) 0.0471(3) Uani 1 1 d . . . . .
H16 H 0.108625 0.346698 1.149548 0.057 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 116.96(11) . . ?
N3A N2A C9 116.5(11) . . ?
N2A N3A C12 120.4(12) . . ?
C18 C17 C9 121.2(10) . . ?
C18 C17 H17 119.4 . . ?
C9 C17 H17 119.4 . . ?
C17 C18 C12 119.5(11) . . ?
C17 C18 H18 120.2 . . ?
C12 C18 H18 120.2 . . ?
N3B N2B C9 112(3) . . ?
N2B N3B C12 107(3) . . ?
C14 N4 C15 117.08(12) . . ?
O1 C1 C2 122.03(10) . . ?
O1 C1 C6 118.16(12) . . ?
C2 C1 C6 119.81(12) . . ?
C1 C2 C3 120.53(11) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
O2 C3 C2 122.17(11) . . ?
O2 C3 C4 118.01(12) . . ?
C2 C3 C4 119.82(12) . . ?
C5 C4 C3 118.84(12) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.99(12) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C6 C1 118.98(13) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.88(13) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 118.46(13) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
C10 C9 C8 118.06(12) . . ?
C10 C9 C17 118.0(5) . . ?
C8 C9 C17 123.7(5) . . ?
C10 C9 N2A 116.1(5) . . ?
C8 C9 N2A 125.8(5) . . ?
C10 C9 N2B 150.8(11) . . ?
C8 C9 N2B 91.1(11) . . ?
C11 C10 C9 119.21(13) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
N1 C11 C10 123.39(13) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
C13 C12 C16 117.80(12) . . ?
C13 C12 C18 115.4(6) . . ?
C16 C12 C18 126.8(6) . . ?
C13 C12 N3A 118.9(6) . . ?
C16 C12 N3A 123.3(6) . . ?
C13 C12 N3B 154.4(9) . . ?
C16 C12 N3B 87.7(9) . . ?
C14 C13 C12 119.33(13) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N4 C14 C13 123.67(13) . . ?
N4 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N4 C15 C16 123.18(13) . . ?
N4 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C12 118.93(13) . . ?
C15 C16 H16 120.5 . . ?
C12 C16 H16 120.5 . . ?
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 1.3586(15) . ?
O1 H1 0.83 . ?
O2 C3 1.3557(16) . ?
O2 H2A 0.83 . ?
N1 C11 1.3334(19) . ?
N1 C7 1.3378(18) . ?
N2A N3A 1.231(8) . ?
N2A C9 1.482(11) . ?
N3A C12 1.491(12) . ?
C17 C18 1.312(7) . ?
C17 C9 1.441(11) . ?
C17 H17 0.94 . ?
C18 C12 1.436(11) . ?
C18 H18 0.94 . ?
N2B N3B 1.241(10) . ?
N2B C9 1.50(3) . ?
N3B C12 1.62(3) . ?
N4 C14 1.3335(19) . ?
N4 C15 1.3360(17) . ?
C1 C2 1.3857(17) . ?
C1 C6 1.3910(17) . ?
C2 C3 1.3910(18) . ?
C2 H2 0.94 . ?
C3 C4 1.3932(17) . ?
C4 C5 1.379(2) . ?
C4 H4 0.94 . ?
C5 C6 1.383(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3772(19) . ?
C7 H7 0.94 . ?
C8 C9 1.391(2) . ?
C8 H8 0.94 . ?
C9 C10 1.3840(18) . ?
C10 C11 1.3772(18) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.3797(19) . ?
C12 C16 1.3901(19) . ?
C13 C14 1.3737(19) . ?
C13 H13 0.94 . ?
C14 H14 0.94 . ?
C15 C16 1.3852(18) . ?
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 2.7579(14) 176.1 . yes
O2 H2A N4 0.83 1.94 2.7734(14) 176.1 2_667 yes
